I'm a local, CT based investor, flipper, and property management company owner.  

If they are asking for short sale that means property is worth less than is owed.

I came across some critical information today that I think is important to share with you:In the aftermath of the LA fires, it has become evident that some homeowners’ insurance claims have been denied or disputed because the property title was held in a trust, but the insurance policy was under the individual homeowner’s name.This serves as a valuable reminder to review your insurance policies and ensure that the ownership structure on your property title matches the named insured on their policy.

Hope is a bad strategy.The only on market strategy that I think can work is paying cash/line of credit/hard money for a property that does not qualify for conventional financing.

For (2), as properties age the rents you command decrease. 

Estoppel letters are definitely something I would recommend for commercial properties.

I should have said that my goal is to flip the property by EOY but rent is this year to hopefully recoup some of the renovation costs 

.#2 - Learn how to run comps so you know the value of the property better than anyone. #3 - Have finances in order (i.e) is this going to be bought through conventional, cash, HML, etc.

If you're looking to connect I am happy to chat about this market and find a property within your goals.

Most likely those would be smaller apartments, sub 50 units.It is harder to find solid property management on the smaller apartments.