I look for a highly recommended mortgage broker and see what interest rates and mortgage products they have.  

At the end of that period, the owner must pay off the existing loan and get another loan to pay off that old loan.

You might check with smaller outfits too like Co/Lab lending, Preferred Mortgage, Aceland Mortgage, and co-ops/credit unions.

I for one built a simple chrome extension to see if the mortgage is less than rent and accordingly provide that information on every zillow listing page.

The comps that do exist seem to be performing at a high-levelMarket Overvaluation?

You are dealing with 2 immovable objects in HUD and Chase and you would be better off with a mortgage broker that would have options. 

A good starting point would be a 10% 2nd home loan or an owner occupied 5% loan where you can convert a basement or studio into a simple 1 bedroom unit and basically let your guests pay your mortgage. 

You have a mortgage on it so no one's going to go after you; you'll just need good rental insurance and (recommend) an umbrella policy. $200-300 per month isn't great, so make sure it really makes sense to keep it as a rental.

A-lister who designs for billionaires and celebrities.In the process of staying on top of our fundraising leads and using our existing fundraising momentum to finish the equity phase and move onto design & sales strategy.

I currently own my primary residence where I am responsible for the mortgage.