Sell or Lease? HELOC available, but GREAT SELLERS MARKET

[Tiffany Koffel]

I recently got married and we are moving into his home, so that leaves my home to figure out what to do with....  

I purchased my home and have operated it as a luxury house hack. The main home is a 100 year old home that I have completely remodeled.  I live in the main home and have a separate 2 BD 1 BA pool house that I rent on Airbnb.  We are in a small town and have a famous flea market so it rents regularly every month, but not all the time.  More like 1 weekend per month and summer months expand to 2-3 weekends per month because we are within a few minutes of a large lake.

I'm a broker so I know that the market is crazy amazing right now and could list my home for approximately $500,000. and could net more than $350,000. on the sell.  However, I'm not sure if that is the best route.  I have considered leasing both homes separately like a duplex and allow both tenants to use the pool as a shared common area.  I would continue to cover the expense of the pool cleaning service to protect my asset as my pool was just remodeled in 2019.  I would potentially rent the property for $2,500. main home and $1,250. pool house.  Here's one more issue to overcome, both homes are on 1 electric and 1 water meter.  

My payment is under $1,800. PITI

I also have access to a HELOC on this property...available $70,000. Owe $10,000.

Would you sell and reinvest in other real estate or keep and lease???