Your income isn't high enough for it to make sense as a rental and the closer you get to your residence limit the greater pressure you will have to sell it before losing your exclusion in whole or part. 500k right now can make $15k per year income with zero maintenance or tenant risks. 

Investment Info:Single-family residence fix & flip investment.

my condolences on your recent lost.there are a few ways you can do this, as mentioned above you can take a heloc on your primary residence which will give you a second mortgage, first mortgage payment wont be impacted. you can do cash out refinance which will give you one mortgage and payment. it will pay the old mortgage and give you money in your pocket to pay for the rehab.or you can do a renovation refinance which is similar to cash out refinance but we would contractor involved  as part of the refinancing and they are paid through the loan

Wife is going into hospice and he wants to move with her, so they're selling their primary residence and some of their portfolio.

Hello,I have noticed that more and more property managers are charging tenants ~2-3% of rent + $30 as admin fee/resident package/utility package.

Quote from @Khon Kounbandith: Investment Info:Single-family residence fix & flip investment.

It is also possible that either the folks in charge of the station, or the prosecutor have set a policy of not wanting to pursue non violent crimes, or even not paying attention to crimes against folks who are not local residents. 

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

I don't know your living situation but if your paying x,xxx for rent or a mortgage and instead by living in one side and renting out the other you will be paying y,yyy instead and y is less then x that's great, especially if you can rent out your primary residence and make income there too. 

Maybe consider getting a p.m. company that would do some boots on the ground and some research for you to find out what some of these issues could be because you are not close to the residence in the location, unless you can do some research yourself online, or consult with the historical Society of the area, look things up at the library, there are lots of different ways that you could start this process, but my point being that you may end up losing more money in the long run.