.- 1031 exchange opportunity: I could potentially do a 1031 exchange to acquire a duplex or triplex, deferring taxes.- Access to funds: I could consider a cash-out refinance or a HELOC to access funds for additional investments.- which property would you recommended me to keep? 

If you never sell, (you will it to your offspring) you never pay tax and they don't pay tax.

Even using dedicated independent contractors as your maintenance crew requires book keeping (bills receivable, payment, bookkeeping to track expenses for tax purposes and warranty claims, etc.).Having a reserve for cap ex, but not allocating any estimate for the cap ex cost means that your cash flow estimate does not include cap ex. 

After two years of occupancy, qualifying for the tax exemption, and benefiting from appreciation, we chose to sell and reinvest the funds.

They might double the 50k or better or lose it all but can just get tax write off and then make it back in one month or less.

He's a CPA with a focus on strategic tax planning.

Property taxes creep up, exterior repairs , and a brand new HVAC last year wiped out $11k of reserves.

Their taxes and insurance may have doubled and they can't afford the house any more.I think geographic is tough because there just isn't typically the turnover any more in most areas. 

You have tax benefits through depreciation and you are gaining experience via property management.  

*Renovation Costs – Includes labor, materials, permits, and unexpected repairs*Holding Costs — Utilities, property taxes, and financing costs during the renovation time.