If you're tax bill is $6-8k (minus the 1031 fees), surely you can make that up by taking multiple swings over a longer period of time.OR pursue some sort of owner occupied strategy with that cash if you can swing a live in flip or house hack.

The demand for rentals remains strong, and with tenant-occupied properties, the risk of vacancies is relatively low.

It had 22 of the 25 lots occupied but we'll be fixing it up, filling it up, billing back water and raising rent up to market.

If i were to purchase a 6 unit apartment for $280K, which fully occupied is roughly $5,050 a month.

You can consider the medium term route as a possbility as well so you can still occupy it for a few weeks a year.  

LLC's are still the way to go but yes you can't tap into owner occupied mortgage tools such as HELOC's or high leverage.

And there are even more carriers who would insure co-living rental w/o owner-occupied - for example Obie.

Interested in getting some extra income with converting the extra space in the basement into a rentable unit.Basements in a one-family home can be lawfully rented only if the following conditions are met:Compliance with the Housing Maintenance Code for minimum room size.There is a minimum ceiling height of 7 ft.The walls, as high as ground level, must be damp- and water-proofed if HPD determines that subsoil conditions on the lot require it.The basement is occupied by one family and does not include boarders.Every room must have at least one window.The bottom of any yard or other required open space cannot be higher than six inches below the window sill of any required window in the room.

Do you want to occupy it a couple weeks a year? 

A colleague of mine has bought two properties owner-occupied back to back in Arlington (with a 5% rate and a 7% rate) doing basement conversions and renting rooms, lowering his effective monthly payment on each property to sub 2K each time.