Estimating rental income is something that I am struggling with when analyzing deals.

If this property is on the MLS, I'd say you may be over-estimating the monthly rent.

I went to craigslist to get my rental estimates and have the realtor getting me some rent comps to be sure. 

I already have been talking to a realtor and mortgage broker, and they have been extremely helpful - just not so much in getting an estimated timeline for getting this done.

After reading your responses to my post where some stated that every mortgage is a promissory note, I had a chance to sit down with a couple of notaries this past Friday when we closed on another few properties.

I can tell you from experience, if by some chance you can negotiate a short sale, if you put one dime in your pocket outside of closing, you could have a roommate and share a bunk in a state facility that feeds you three times a day.

Any chance of holding as a rental until day 366?

Howdy @Christopher V.Based on your $300K ARV and $75K Rehab estimate I would offer something like $120K - $125K.  

@Sean OToole and @Christopher Phillips - Here's a quick note on getting a sellers list of owners with equity:Loan to Value (LTV) is used as a tool to estimate equity.

personally I would wait. why take the chance?