The overwhelming majority of tax liens are ultimately redeemed, so buying in your name in search of anonymity down the road shouldn't be an issue. 

Check out my page, I'm new to BP but have linked our social media & I enjoy working with investors like yourself. 

We are thinking of doing something like that but wondering if the people will have issues with who spends most.

I also would add that even with all of that you can have issues with a tenant.

Had a similar issue once with a hot tub and I installed multiple shade sails to block the view ... people are crazy

Plumber mentioned there is a ejector/grinder pump in one of the units that handles all sewage from all 4 units.They replaced the ejector pump and in 2 weeks, same issue happened with the sewage leaking in the garage.

When viewing potential purchases pay attention to any damage such as cracks, leaks or structural issues; you may want to hire a professional inspector for extra assurance.

It is not an issue if you are adding more square feet for your personal preference, but I would not expect an ARV that is as high. 

Tagging in @Chris Mury as he knows a lot about airbnbs in St Augustine

Any tips on dealing with these issues.