@Nicholas Pisano real estate investing is a long-term game, not overnight.Have seen many newbies jump in a buy several properties, then when things don't go according to their unrealistic plans, freak out and sell at a loss.A past client is doing that right now - they bought 5 properties from a high-pressure agent, hired us, micro-managed us to try to meet their unrealistic expectations, terminated us and hire another PMC to "save" their portfolio and went that didn't work out, are now selling 3 at a loss. 

You can try it if the electric costs don't work out. 

And honestly I'm kinda worried about how it all goes due to my current lack of knowledge, but I'll do my best to make it work out no matter what.

First, you may not like being a landlord, so figure out what you want to do if being a landlord doesn’t work out.

Long story short, we will see more people not using buyers agents and they may work out once in a while but in the grand scheme, they'll get what they pay for.

Knowing the future structure is good and planning is also good, but if you are spending the majority of your time, as it said, on structure and not real estate, your reps are being put in the wrong workout bin.

I don't know that I would gamble and say you could sell it if it doesn't work out, you could be holding it for some time.

Quite frankly I would be inclined to turn down investors at high LTV, but owner users seem to work out.  

So, you have a back up if STR doesn't work out.  

My approach is probably fairly unique in that if the homeowner wants to keep the house and would traditionally not be able to, I point them in the direction of their equitable remedies and have had success helping folks keep their house and work out a sweet deal with the finance company to boot; I've retained a minority equity stake in the properties as a result.In the case where it's a non-owner occupied property and the investor no longer wants the headache, I negotiate either an acquisition in trust of the LLC/Corporation that is holding the deed, or have the deed quit claimed to me individually.