Also there's the headache factor with investing out of state especially older homes. 

But with our tax guy retiring this year, I'm thinking it's probably a good idea to bring one on eventually, someone that can advise more thoroughly on this and other issues as well as file taxes.I still wonder if filing seperately could eliminate some of the headache we have with his ex.

Every month your property sits empty is money directly lost from your cashflow. But vacancy is not inevitable. With strong property management, it can be significantly reduced while maximizing profitability
1. Effect...

Hey BP community, I could really use some perspective from folks who’ve been here.
Here’s our situation:

We have one rental property (premarital, in my name) and a small attached unit in our primary home (joint title...

That headache is being passed on and there is no set standard as to how much of a discount that is.

Pros: higher cash flow, guaranteed rent from the housing authority as long as you’re not in violation, tenants usually stay longer than private renters, and the regular Section 8 inspections help keep the property in decent shape from the many inspection reports I've seen.Cons: Inspections can sometimes be a headache, delays move.

If it’s too much headache I’ll just keep it and rent them.I hate losing the 2.625% 30-year fixed mortgage.

If you already don’t want to self-manage, I’d say look at friendlier cities; the headaches in strict ones often outweigh the returns. 

Comping properties has become a bit of a headache for me due to its ambiguity.

I have a motto: "the smallest deals come with the biggest headaches and smallest pay days".