And while your homes might be an alternative experience to hotels (which is awesome!!!!)

Insurance is paying $7000 to redo roof from wind and will cost me $1500 in materials and $1000 in labor. 

The deal is almost in the purchase price.I used to work for institutional asset management and equities and alternative investments do have a place in your investment sphere but for me, real estate has been the only thing that allows me to "not work" when I don't want to.I do also take advantage of solo 401k which allow you to put 50k+ per individual tax deductible every year so I am still heavily invested in the market. 

Looking for some advice, alternative options and or ideas... thanks

:Pwasting my raise money on too many material things

Additionally, there is a lot of great material in the forums on pulling home equity for your primary residence for down payments (home equity loan OR a HELOC), you will be hard pressed to find one that will do that on equity in an investment property though. 

Of course I will disclose the material fact if I sell. 

In his materials and podcasts, @Brandon Turner discusses that he's managed all his own rental properties even when he had units on a large scale. 

I have read a lot about advantage of claim "active participation", but no article about any pros on NOT claiming active participation.I have placed a couple of properties in service in 2019 and will have a loss that can offset up to 25,000 active income assuming i claim active participation (I am not a real estate professional and I know I cannot claim "material participation").

Looking at it from another way, if you do the deal and your worst fears do come true, what's the downside to you and do you have an alternative to selling?