During this period I want to get comfortable with a PM software that is both landlord and tenant friendly.

I'm sure there are deals to be had but I'm not comfortable with this process.

IMO you have two options, be completely comfortable with the math, learn them in and out and then do a deal OR do a deal, hope it works and then ask us after why you lost money.

There’s deals to be had and fortunes to be made in c and d class neighborhoods if you have the fortitude and you are willing to step out of your comfort zone .dont sit on your laurels and think you need to wait 5 years and borrow 200grand to get ahead in real estate .

You should be calling the shots and using whichever agreement you’re comfortable with.

Been an owner for 4-5 years, learned quite a few things already, among which is that a commercial kitchen is not something to be made or modified lightly - it has to be properly designed and properly made in order to function well.So I have this retail store of about 1100 sqft that someone wants to take for a small coffee shop with the ability to bake.My question is where do I start searching for someone to design/compute small walk-in cooler, grease trap, vent-a-hood, stove and HVAC on top of that so all this could become useable without anyone getting burned.From my past experience I have local mexican crews who can do any and all of the listed things and they'd do them relatively well except they won;t ever be designed to actually work well together.On the other end of the spectrum I've worked with american general contractors and they tend to cost 2-3 times the Mexican crews and, at least in my case, ended up delivering about same end result (in all fairness it was only kitchen remodeling, not design from ground up; but statement stands valid and I was able to later do almost the same at literally third of the cost).Your expertise is appreciated.

I made the same argument at first as well for someone with multiple rentals (As I do for like...home office deduction, if you're managing 5 rentals, collecting rents, screening tenants ect...I am comfortable taking that deduction- I was going to apply same here but saw a no aggregation wording) 

I feel like in a market of $1800 apartments and $350k 'entry level' houses, there would be a huge demand for $1200-1400 rentals and sub-200k new homes, even if minimal in sqft and design.

I bought the lot 10+ years ago to prevent a slash-and-burn developer from getting it and putting a home that wasn't right for the historic neighborhood (it's not designated, modern homes look extremely out of place here).  

If it’s as simple of a size and design as you have stated just do it yourself .