I ended up investing out of state in a more landlord friendly / cost effective market.First thing I'd recommend is figuring out your investing strategy (single family / small multi-family 2-4 units) and attend some local meet ups to network with other investors to learn from their mistakes.

As a PM I can justify the cost of this software, if I was self managing 1-2 units I likely would not. 

A generic program can’t be tweaked enough to make it effective for any particular deep niche.  

We (my wife and I) have been at it for a few years - self managing mid and short term rentals.

Do you self-manage?

This will effect your ability to obtain financing for quite a few years but may be worth considering.  

It is not going to be cost-effective to run a vent for a dryer.

What makes it slow in this case is that you don't really start seeing real cash flow until after year five but it's more effective than rentals in that there is little to no maintenance.Sure you can live in a home while fixing it up with the intention of selling it for a nice profit later but I think many people are already doing that and the buyers of slow flips now also have that opportunity without having to qualify with a bank.

Companies self-certify on a one page form to INC.I wouldn't describe any of this as "conservative."

Hi Randall-Congratulations on buying a rental property well back in 2020.I am sorry to hear the property is now cashflow negative $200 a month.Your question is should you sell or continue to keep it with the negative cashflow.Depends on your personal goals and if being negative $200 a month plus any unexpected repairs or vacancies is affordable to you, but if you can solve the negative cashflow by turning the property into a furnished mid-term rental, for example, your future self may thank you.To Your Success!