I can utilize dependent care savings account under my employer, and also contribute the residual PM earnings to a SEP IRA or solo 401K for my spouse.

The deal will have several interdependent factors -- mainly, 1) the sales price of the business, 2) the RE sale price OR lease deal 3) the employment agreement for the key employee (my spouse) who would be required to work for a couple more years after the sale. 

I’m not super savvy with the market there and I know a lot of it will depend on the university and major employers there (hospitals etc).

I have worked with the GC, I believe his name is Dave, on a few projects for my current employer.

To the extent that your net is a loss on the property because of excessive depreciation, you can only deduct the loss against W2 income if you (or your spouse) are a real estate professional (and file jointly), or if your W2 income is $100K or less.If your spouse is not employed in a W2 job they should generally be able to qualify as a real estate professional if you are self managing an STR but then your spouse actually has to be the person doing the STR work... 

As you can imagine, the home needed a lot of work, and without a ton of capital, my Mom (with my assistance) employed the 'sweat-equity' approach.

If you're 1099, you can also look at a bank statement program which is specific to self employed individuals (once you have 2 years experience).

I am not aware of any investors who employ this strategy over a long period and make money buying cheap turnkey houses.  

I currently have a 401(k) with my employer.

I employed a “career starter loan” that was originally 36k to pay closing costs on a VA loan for the initial purchase.