But at least you're getting a wash instead of getting screwed.As my colleagues said, Form 3115 is not a DIY project.

I can do title research on my own, I've dealt with property management companies, and I've dealt with all kinds of real estate related litigation (adverse possession, title defects, foreclosures, HOA disputes, evictions, to name a few).

One challenge to manage is being able to clarify for lenders on those rentals (if you have them) which amount of the premium should be paid for each rental so that they do not include the entire premium into their escrow analysis, inflating your monthly payment on that rental. 

Acquiring your 2nd STR is predicated on your successful acquisition and management of your first, and there are a lot of practical skills to learn on #1.  

For example, one $27/hr FT property manager of mine can manage 140 leases.

First thing I notice is the big jump in ARV from the Total Project Costs.

Do you think purchasing a property in Philadelphia, PA, and managing it remotely from Westchester, NY (Roughly 2-2.5 hours away) with the help of a local handyman would be too much of a stretch?

I'm the member and manager of Skeeters Residential Renovation Services LLC 

I'm looking to connect with local investors, agents, lenders, property managers and contractors who have experience in these areas. :-) 

Agents and property managers are easy to find on BP.