Hi @Jonathan Yi, just a quick tip about getting work done on a Condo:  Check what the association requires in terms of insurance from the contractors.

I own an insurance and financial practice and could not justify the cost of the license, time required, legal concerns with REI, and overall cost.

I got fined on that one .to get the license you need a bond and insurance..  

The duplex's and Tri's in my opinion do not cashflow as well, have weird valuation histories, and mostly trade to owner occupants where 4 families go to investors and sfr's can be exited to homeowners.  

Pretty much standard windstorm insurance is about 5% so that would be about 20K. 

Overall, they are giving me 15 days to close.Service link is offering title insurance, but I am getting the following phrases from Hudson and Marshall.."

College town properties often require investors to budget for higher insurance and repair costs.

Any idea about insurance?

But I think I would rather be in, increase rents increase value then get back out before any major work needs done.It would cash flow positive as it sits after mortgage, taxes and insurance.

A successful short-sale typically benefits the borrower (homeowner) in the following ways: it can give them more time in the house (and payment-free); it is better than a foreclosure from a credit report perspective and wold allow him to obtain a new purchase loan for a new home in the future more quickly as compared to having it go through foreclosure.I would encourage you both to reach out to a local realtor with short-sale experience and have them facilitate the transaction, it would not cost you or the owner the commission as it would be paid out of the bank's proceeds.No, in a short-sale I would definitely not offer any payments to him directly that are not known and approved by the bank, you can get yourself in hot water and probably legal trouble by doing that on a short sale.