However I really want to get into the property management business as a side job and since i plan to manage my own property, I figure it makes sense to throw a few others into the mix since I'm already doing the routine.

Buyers routinely ask for seller to pay closing costs.

I don't have a calendar of when I should be doing routine maintenance however. 

I have social anxiety and get very uncomfortable in group settings.

If you feel uncomfortable disclosing all this information in public, send me a message.

Even coming up with the 20% down payment on a single family home would be difficult for me.Building seems to be a good route in my situation because the comps on a 4 unit building in SWFL are routinely $400,000 and up.

@Daniel Mendez yep...pretty routine stuff...you just want to chose your lender and loan product carefully...make sure you have this lined up before you do the deal.

  :)    Gives me a heads up on routine stuff like roots, obstructions, etc, to clear.... or that I will need to dig the whole thing up because its crushed or built out of tar paper (look up "orangeburg pipe", it was a thing back in the 60s!) 

But when the investors are your family, those nice family get togethers become this uncomfortable situations where you know they're looking at you and thinking about the money.When everything is sweet.

Call in the HVAC guy to do routine servicing of the unit to make sure it's running correctly; cooling adequately if coming into summer; coming on if you're getting into winter.