He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

lastly I think the sellers in these areas are far more sophisticated than inner city rust belt property owners about values..

Once you're ready, create a goal (e.g., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

I have great lenders and property managers I can refer you to.In Cleveland, it all depends on what your goal is.

It seems a traditional sale gobbles up half of it in closing costs.We refinanced early last year, and another refi would cost ~$5k, plus w/ the LTV, I don't think the numbers work out just right.Too bad we were too naive to even consider those offers when they were handed to us.

It's a balance of cashflow and wealth accumulation.One of the goals is to have tenants pay as much of your cost-of-ownership as possible (loans, taxes, insurance, etc.)In high-cost areas, any Class A or B property you buy will usually negative cashflow for the first 3-5 years, until rents rise enough to cover the negative cashflow + rising taxes & insurance.Investing OOS increases your risks because you may not know the market and you can't check on everything/everyone all the time.If you move forward with your buddies, HIGHLY recommend creating a solid Partnership Agreement!

At this stage, the main thing we need is for me to get back into the workforce and get some money coming in, in order to achieve that dream.With that in mind, my immediate goal is to gain employment in the field of property management, as opposed to wasting my time working in another field that is not associated with real estate.

I have 0 experience ground up construction loan program nationwide that does NOT require GC to sign anything, only provide proof of 3 C/O's (certificate of occupancy) over the last year I.e. built received occupancy permission now unit is on market or habitable. 700+ FICO I can get you 80%LTC loan to cost on the project on ground up construction for 1-4 units.

Why would you literally wait until the last minute, when a flat tire or difficulty finding a parking space be the difference between keeping and losing your home?

I agree with @Ashish Acharya if you're interested in reinvesting the proceeds into another investment property and your goal is to minimize your tax liability a 1031 would work out well for you.