And yes, for $10k I will travel to MA, been wanting to see that part of the country anyways haha.

One of the dangers of listening to a lot of personal finance advise shows is that you get conflicting advice, the advisor doesn't have experience with the personal issues you are facing (like pregnant wife/girlfriend, child with medical issues, irregular income, job might go on strike, etc...), or they really need to sell you something to pay their bills.

This allows time  for travel and of course the grandkids. ;-}

I disregard student loans and medical debt.

I travel a lot so I'm suspecting I'd be there 80% of the time. 

There is a lot of the retail sector doing great right now (auto stores, Davita dialysis, most medical, grocery store, dollar store, some QSR with drive thru, etc.)  

I might be inclined to share a little secret here... if your STR is currently in a Covid Zone: consider trying this: - Convert all listings to a 1 month minimum, by the room- Add all appropriate features to suit this- Mark the price up to 2-3x the typical rent, including everything- Sit back knowing that at 50% occupancy your roughly breaking even- Watch as your life gets really, really simple... as you have to work less and less every day, allow your net to drop to about 50% for a while, knowing that you are reducing the risk of Covid spreading in your business, and knowing that you are creating a safe space for those people who were planning to travel, but just want to chill while humanity finds a cure for this thing. 

@Sharron Martin I just want to say that I'm so sorry to hear about your divorce and your medical issue.

We are actually looking to do things a little backwards and pick-up a small rental property within the next 1-2 months that we can fix up and use while traveling back and forth from Chicago to Atlanta to learn the area and prepare for our move; and then rent out the property after we purchase our new home.I'd love to learn about current areas that have potential for buying in low now, rent the property out after we are done using it, and then selling in 10 years with substantial increase in equity.

I also like to travel, and I do not want to have travel plans dictated by client schedules.