@Joel Scarboro Many cost segregation companies will provide you with a free cost/benefit analysis quote so you can get a better understanding of the cost and the potential benefits available.

Important to note, I am provided full access to all of the meetings and pre-development functions to grow my knowledge base while I am getting my personal financials in better shape to purchase properties I view as better long term investments. 

if your goal is cashflow, but you don't want to self-manage a STR or MTR, then selling to make that equity work harder for your somewhere else is the only thing that makes sense. q: would your time be better spent focused on flipping & letting that rental break even, or going through the process of turning that equity into cashflow via a 1031? 

Even if they only clean when you are coming thru, that is better than years of piling up.5) Gives you information to determine if you want to renew the lease.6) If you have regular inspections, then if a tenant is withholding rent, it gives you the opportunity to check on your property.Older homes with radiators and no fans in the bathroom are a nightmare.

However, based on what you stated your goals are I think buying the next house sounds like a better option to reach those goals.  

Because they are §1231 losses they can offset ordinary income, which is better than a normal cap loss use of only $3,000 if married.  

The lot is steep and we had an architectural engineer outline how the cost to remove boulders and build up high (where there would be a better view) would be quite substantial but building lower by the road was more feasible.

There are definitely better creative finance options out there. 

Wow Emma, I couldn’t have asked for a better or more detailed answer.

I took a trip out to Indianapolis just recently to get a better sense of the neighborhood and you are definitely right about it being block to block.