This past year there has been no issues renting the property, but the old windows definitely seem out of place compared to the rest of the house. 

I currently have two past residences (SFH) that I rent out totaling Jon Thx, Jon. 

That's why we do our due diligence, employment screening, past residential screening, etc.Talk with the applicant, be upfront with them, get to know the person(s).

In the past, I've not had any issue getting investment loans and found it somewhat odd they are looking so closely at my personal income, but so far this has been my issue.Does anyone have any recommendations for how I can go about finding a lender that will work with me based on the equity and cash reserves I have?

I have been consuming as much information in the past two weeks as possible on this site (and others).

For the past 4-5 years, I've been hearing people say the market is going to soften or crash, etc in this town.

I get that question a lot and did a podcast episode about it the past few weeks.

He basically has had use of the property for the past seven years with no rent obligations.

I have tried in the past to do this with a solid written agreement spelling out exactly what the terms of the agreement were, what was to be done, and that the work needed to be completed in a professional, workmanlike manner.

I've been trying to learn all I can about this for the past 6 months and am now starting to take action with what I know about it so far.