Interesting thread.

I sell deep out of the money short premium on both sides of the major indexes all the time. Primarily the S&P and Russell 2000 cash settled indexes, but if there's good risk/reward, any underlying is fair game. I start closing out contracts at 50-60% of my max profit and rarely if ever hold to expiration. Contracts that move against me and wind up in the money get rolled out to the next expiration cycle.

I also have a buy and hold strategy for what I refer to as "change the world" stocks. I'm in for the long haul with a select few companies that are doing things that change the way a significant portion of the world does something significant in their lives. I only sell out of these positions when either a) the company seems to be changing course in some manner that looks like a long term negative OR b) the stock has become so overvalued that it's unlikely it's numbers will EVER justify it's current price. It's all a crapshoot of course, I bought Google shortly after it's IPO and sold at $285 thinking that was all the money there was to take off the table.... Shoulda held that one a little longer.

As a young carpenter starting out many moons ago, I quickly realized there was no pension plan in my line of work and most of the guys over 40 were working in pain every day because they couldn't afford not to. Bad backs, blown out knees, etc were all too common for my liking. So I started buying up land when and where I could find it in my spare time and building rental properties on it during the slow season. Taking that path has been good to me, so I try to pass on anything that I think might be helpful.

I would say that "typically", you're going to cashflow more on a per unit basis with multi-unit properties as compared to single families. That, however is a very broad statement that has a lot of factors that can change things, such as the purchase price, financing rate, state of repair, local tax rate, occupancy rate, etc. But a dozen units under one roof has always provided me with much more free cash flow than a dozen single families, for less work on my end to boot.

What jumped out at me in your post was the assumption that moving up in size of property means accepting a drop in resident quality. There are good, hard working, decent people in every area and at all income levels. A good resident screening process makes all the difference. That and being willing and able to keep a unit vacant for a month or two if necessary to find the right new resident. A bad tenant is MUCH more expensive than a vacancy.

Our screening process begins with our ads, progresses through the phone interview, viewing and application process and is designed specifically to have the deadbeats self select themselves out of our process so we don't have to.

The next step after finding the right new resident is keeping them, and we've also worked out some simple things that help on the retention side. With proper screening and retention techniques, we've been able to get our average occupancy to 7 years as of now with a goal of getting it to 10. That's in both multi unit and single family, while keeping rents at market levels, with very, very few rent collection issues.

Of course a bad tenant slips through the cracks now and then, and a good resident occasionally turns bad, but that's an occupational hazard I'll take over climbing around a frozen roof in the dead of winter every day of the week.

Since you seem to be interested in gaining information/experience on the operational side of this business, I'm happy to share our ads, phone interview questions, application, etc, as well as explain our reasons for doing things the way we do, in the order we do. But it's a lengthy conversation best taken private. PM me after the holiday's are over if you're interested.

Also, I'd recommend Jeff Taylor's stuff over at mrlandlord.com. At least on the operational/tenant management side of things. Several years back, I booked into a conference he held in Orlando that was strictly about managing property. My intention was to get the write off for a preplanned vacation. We were going to Orlando, so why not? I didn't have high expectations, but I found our management philosophies very closely aligned.

I want to echo what Dave has said here. If you know something others either don't know yet, or haven't acted on, and you REALLY know you know it, find a way to take action. One or two deals can set you up for life when timing, circumstances and knowledge come together.

As an example, I've got several apartment buildings sitting on lots that were originally zoned for single family homes. I purchased them based on their value as a house lot. What I knew, from actively buying, building and developing in that general area, was that obtaining a "development agreement" (the term used in our area for a zoning change) on those lots for multi unit construction was highly likely.

Those purchases worked out very well and confirmed forever for me that it's worth the skullsweat required to figure out how to pull a deal together.

There's some dang solid wisdom right there.

tastytrade.com will supply you with a shitton of education on the world of options and other derivatives free of charge. But for the love of God, spend some serious time either paper trading using one of the platforms that have that built in (thinkorswim is one for example) or trading extremely small (one contract max trading size in lower value underlying securities) until you've got some real world understanding about how it all works. It's a very easy place to go belly up quick.