Owning a rental home with or without house hacking is a pretty basic thing that almost any certified tax professional or accountant should be able to handle.Think a little in a bigger picture about what type of advice you will want: tax, accounting, financial planning? 

But you need to learn all about landlord/tenant laws, how to do basic repairs, know what average labor and material costs are for common projects. learn about payment systems, how to interview property managers, tenants and handyman services, build a team of realtors, contractors, title, hard/private money lenders, inspectors, appraisers and soooo much more. 

.- Invest in 1-2 smaller mulitfamilies (2-10 units) and drive up the value so you can pull out your cash and find another similar mulitfamily property.- Co-GP or partner on a larger syndication or JV purchase of a large multifamily.

I did basically push one incompetent appraiser out of the San Diego market because his appraisals were so bad he was getting the reputation he deserved (I won 2 large appeals and he left when I was appealing a third which sucked for me).  

I have basic question that I'm still unclear on.

If you are so broke that $200 is killing you, drive some Uber for a while.

So we have 3 buckets in my mind - SFH sale (basic), developer sale for the size of land (new to me), business sale (home + business).The most value would be in selling home + business I believe but I have no idea how to market/find potential buyers for such a thing.

The only reason I can think of is to cash out all of the money they made and put the risk on investors and basically sell it at market value to themselves..... 

Basically, just run deals in your market even if you're not planning to buy.

And any loan basically at 65 to 70% LTV total if the first goes bad your going to take a huge risk of loss of interest ( almost guaranteed) and loss of principal..