and... unfortunately it actually takes money to flip. 

In actuality the lender won’t lend because title companies won’t offer title insurance until the 2 year period expires.  

Its a win for the tenants only paying for utilities that they actually use, and a win for you as owner reducing your expenses, & eliminating your risk of utility cost increases. 

From their website:      Maryland 10% to 14%Actually Maryland is 8%  up to 20%.

I can't talk to family or friends because everyone around me thinks i am doing better than i am actually doing (or should be doing).

I want to house-hack a duplex but I am not ready to actually move out of my parent's house because of sick family members.

You could research and try to take advantage of he STR tax “loophole” but you’re simply accelerating your depreciation deduction not actually reducing your taxes. 

I'm actually excited about the prospect of finally owning some rentals, as I've wanted to do it for a long time but I let life get in the way. 

In this case, the taxation actually occurs on your tax return. 

Having a completely separate credit card just for this purpose, and even if you don't go for a specific software yet, since you are still on your first building, actually being diligent about tracking in a spreadsheet will set you up for success.