These are all STR communities that have similar amenities, close to Disney and have various sized homes that do well in the STR space. 

Well worth it IMHO given poor performance of RTO/seller financed zillow listings. 

I'll just add that in addition to offsetting future tax liability, I'd like to offset current taxes as well, during my highest earning years. 

My mum currently lives there, she is 80 and not very well, but you would also become a tenant in common and as such if you had the time you could profit 100% from the transaction, as I need cash urgently and am willing to heavily discount the asset.I am wondering if there is a market out there where someone wants to get a foothold in the London market by buying my part of the property.

However if you have enough reserves, 6mo or greater then I'd say chance it but a couple of missed payments from the tenants and you have to foot the payments out of your own pocket.I'm all for taking risks but I think you really need to evaluate the age of the major systems so you don't get hit with a bunch of cap ex all at once as well as your reserves. 

I also invest in other assets such as stocks, and private companies as well.

I highly recommend a well-qualified REALTOR who works with investors and knows how to help you best.7.

Well if you ran realistic conservative numbers for maintenance, capex, vacancy rates, rental income, etc then you don't really need cash flow do you?

I am open to other markets as well. 

I love sub-to deals and have done many of them as well, but there are risks and they need to be done with all the proper docs & paperwork.