I will wait to hear from the more experienced pros as well.

Do you guys think that this deal would make sense or should I wait for something that I could cash flow on even with occupying part of the residence? 

Still in the early stages of conversation but got some beginning information and wanted to see if this was worth pursing:Asking Price: $550,000 (I already assumed that was too high, trying to figure out a reasonable price to offer)Income: $4000 a month (believe there is potential for rent increase (waiting on specifics of each unit))Expenses: $900 a month (Water, Garbage, Taxes, Insurance, Maintenance, Pest, & Septic) Self- ManagedNOI: $3100 a monthCap Rate: 8.72%Stable TenantsDoesn't need major workGood Area, Decent SchoolsQuestions:1) What is a fair win-win offer?

@Matt Fore Yes it does have to be capital gain although there is some language that just references "gains" so we are waiting on additional guidance as to whether ordinary gains would qualify.I think the reason capital gains need to be invested into the funds instead of straight cash is that by recognizing a capital gain you are selling something which promotes economic activity (selling stocks, businesses, real estate, etc.)

I was just curious if i should go ahead with it or wait until spring when I’d likely be able to fill the house quicker.

Wait so it's been working for a year since when tenant messed with it?

I don’t want to be one of those that throws up a number and wait for someone to bite the deal.

The first time I scheduled a meeting with the owner to discuss rental remodels and when I showed up for the meeting he across the street to eat and told the secretary to tell me to wait (on the phone).

Bleeding thousands of dollars in one go on pest removal, tree removal, mold removal.

Personally, my favorites are...ABCs of Real Estate Investing by Ken McElroyWealth Can't Wait by David Osborn and Paul Morris (about SO much more than investing, about life and it's amazing. both have appeared on the podcast)and you can't go wrong with Brandon Turner's books.Best, Derek