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. 

that COULD BE looked at as your COCR in moving around this equity. but to answer your actual question, it depends on your long term goals. if you want a million units you'd be better off in multifamily. if you want a small but mighty portfolio that you're always optimizing, maybe have some STR some MTR in there, self-manage, keep it simple... you could stick with SFH and probably have an easier time managing.

Insurance is dicey and it's better for me to spend $100K than saving that by using insurance but risking no renewal...

Its even better sometimes because its on their money, not yours.