Quote from @Nathan Gesner: Unkempt lawns, trashy or broken down vehicles, mattresses and trash on empty lots, boarded up houses, bars on windows, dealers and hookers on the corners, the lack of stores or gas stations, occupied properties are dilapidated, etc.Or when Google maps shows stuff like this: Bro, take my front yard off the internet.

Fannie Mae has a requirement that if you want to use the rental income from the non occupied units, that you MUST have a current housing expense which means you cannot live rent free.

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.

Everyone thinks they can paint but there's a big difference between a professional paint job and a non-professional one (the latter usually actually damages the property instead of improving it). 

Id keep looking if it was not an approved short sale ( even an approved short sale takes a very very long time and theres no guarantee that you will even close on the house after months of waiting). q1)There are plenty of non traditional lenders that could offer you construction financing if the numbers make sense but it will cost you with points and a higher rate.

HUD does a non interest bearing 2nd that you might want to consider doing.

I currently am a resident here (so distance is non-factor) and I possess some handy skills that could save renovation costs (besides HVAC, structural issues, plumbing, electrical work).

The internet was a viable platform back in the '90s.

This allows you to access funds while keeping your existing mortgages intact.Second Mortgage: Explore lenders who offer second-position loans on investment properties, though rates will be higher.Cash-Out HELOC : While traditional banks often restrict HELOCs on non-owner-occupied properties, some portfolio or private lenders may offer HELOCs for investors.With $15-20K in liquid funds, look for deals where you can negotiate terms:Seller Financing: Negotiate lower down payments or interest-only periods.Subject-To Financing: Assume the seller’s existing mortgage while covering the down payment.Lease-to-Own: Lock in the purchase price while using rental income to build equity.

Our pet deposit is non-refundable which is what I generally would recommend (assuming your state and local laws allow that).