What it seems like you are doing right now is stretching and rushing.You have a good nest egg for your annual salary, you don't want to burn that all and have to wait a few years to build it back up again.

If a STR has a typical homeowner's policy and just Aircover, and the property burns or a tree falls on the home, it will not be covered at all because it was operating as a business under a homeowner's policy.  

I think house hacking is the easiest way to build wealth over time and I would hate to see you get burned out on a riskier investing strategy before you get started

Quote from @Cassidy Burns: Hey @David Cherkowsky , my advice is that if you do live in the DMV, you should try to at least purchase 1 asset while you are here.

If you are going to wholesale the property, try not to blow smoke and say you need to have your partner come look at the property before closing - you are wasting the seller's time and many have been burned that way. 

Be aware, you're going to burn through handymen pretty fast.

The plumber came back saying the either the pump was burned/failed because of too many wipes being flushed down or when "an outside vendor" did snaking the pipe, it damaged the pump.He also mentions the "pit" where all the sewage from the fourplex comes to is too large, corroded and needs to be fixed:"using gravel to fill in the existing voids present aroundthe pit, then install a new pit with the extension lidneeded.

(i) Tenant is responsible for all damage caused by smoking including, but not limited to stains, burns, odors and removal ofdebris; (ii) Tenant acknowledges that in order to remove odor caused by smoking, Housing Provider may need to replacecarpet and drapes and paint the entire premises regardless of when these items were last cleaned, replaced or repainted.Such actions and other necessary steps will impact the return of any security deposit.B.

I knew for this to work I had to put in the time and have that burning desire to make it all work.

burning pallets in a firepit so you have 9000 nails to dig up when they leave.