I've been using Hostaway for a few years and generally like the platform and the support.We made a recent switch from Turno to Breezeway for better vendor/maintenance coordination.

That gives them plenty of time to collect and transfer everything to you.

There were some years ago when buyers would just take over the lease and that is it, the value stayed the same and it was transferred in escrow to the new buyer if they qualified. 

@John Kelly You’re right that transferring your homesteaded property to an LLC can often disqualify you from the homestead and veteran tax exemptions because these typically apply only to individuals, not LLCs.

Coordinating OOS deals is hard. 

When selling for sale by owner (FSBO), ensure all legal documentation is in order and consider consulting with a real estate professional or attorney to handle the lease transfer and legal aspects effectively.

I’m also currently looking to upgrade to a software that allows me to transfer friends from PM to owner and will help me generate form 1099at the end of the year.

That's a spreadsheet that doesn't transfer to a real life leasing scenario because its not permitted within the zoning code.If the property is zoned RM1, then  perhaps you can lease to 8 unrelated individuals by converting the building into multiple units.

Consider transferring to an LLC after occupancy, keeping the due-on-sale clause in mind.This post does not create a CPA-Client relationship.

@Charlie Martin Buying under an LLC offers liability protection and separates business finances, but it can complicate financing with higher rates and stricter terms, and lenders may still require a personal guarantee, impacting your DTI.For your first property, consider purchasing in your personal name for better loan terms and transferring it to an LLC later if needed, while using strong umbrella insurance to mitigate risk.