If the mid-term rental wasn't the issue, then i'd move on to my next point.Again, assuming you aren't burdened with the uncertainty of massive repair expenses on the other property, i'd assess the rental value of the condo you're living in. 

I'd vote against refinancing into a higher rates unless it truly makes sense. 

@Ryan Williams Nice job, Littleton is a fantastic area for house hacking, just takes the right investor to see the potential, and I know that duplex, and there is plenty of value add for your client.

While I'm there, I'd love to meet up with an agent or broker from the area and talk about being referral partners. 

Honestly that many homes and long distance management, I'd start selling some of them off starting with the ones that are the biggest problem. 

I'd rather go change a lightbulb myself than pay someone else $100 to do it.

But for investment properties, I’d feel that would open us up to way too much liability that insurance likely wouldn’t have to cover if a tenant or guest was injured where a permit was required but not obtained.

I’d suggest talking to the city to see what the zoning allows for from a use and density standpoint.

I'd love to connect with anyone based in Philly or has experience investing in the market!

There are plenty.