The process of converting the building to a condominium requires filing a master deed and establishing an HOA in order to end up with four separately deeded units that you can sell off individually.When you're ready to begin the conversion, I'd suggest pursuing financing that is tailored to that strategy as standard loan documents will not cater to your plan.

Any input on Accounting Software that is easy and kinda of tailored to STR - or rentals?    

I'm mailing in the Silicon Valley, a.k.a. the Bay Area in California where there are very little foreclosures and motivated sellers so our letters need to be tailored to people who just want to sell their homes without going through the drama of an open house.When ordering, I noticed a lot of different options like having an actual human write your addresses vs just using a handwritten font.

If you already have a realtor I would just suggest a tailored search set up through the MLS that is geared towards your investing strategy which our area's MLS has this ability.

I have taken my car to bad mechanics, gotten bad haircuts, bad tailors, etc.

I do not tailor pick deals for clients (unless they have taken care of me) because you could choose to pass on it, and now it's too late for me to send it to someone else. 

There's no one-size-fits-all blanket strategy that's best.The best strategy will be tailor fitted to the individual. 

Are you going to tailor your life to the lowest possible taxes?

This will alter your strategy and how much equity over the years you can pull out of the properties so it needs to be tailored to the market that you are targeting.

There's nothing wrong with the "rules" although they are actually called "rules of thumb" which means they are a general guideline.The 1% rule has to be tailored for your market.