Besides comprehensive lease agreements outlining the tenant’s property maintenance and damage prevention responsibilities, I am also thinking about signing with a tenant's additional agreement with all prices for typical damages which they need to sign with a lease.

Even so, are there are other considerations like family or significant other that prevent you from considering a move like this? 

Natural disasters, higher construction costs, and a competitive insurance market are driving these increases.Review your current policy to ensure you’re properly covered without overpaying for unnecessary coverages.

We are in a reverse frog boil environment  - Instead of boiling to death slowly they raised IR so fast that people are unsure/unclear when it's a good time to come back in - they will more than likely lower rates 1/8 to 1/4 point at a time, incredibly slow to allow the market drip back to normal preventing a surgeI'm also seeing people drop $5,600,000 in cash to $13,000,000 in cash like it's nothingCash rules down in florida even on 889K deals 

Your rent of $800 is really reasonable, my advice is still to continue increasing income, decrease other expenses (cancel unnecessary subscriptions, cut down on going out, all those little things add up to a lot.)

Having the tenant  makes it:A) harder to show the property, making it harder to sellB) prevents a majority of owner occupant buyers from being able to offer on the home.

I believe it tends to give me a slightly lower return, because the sponsor is going to be more careful, and if there is a severe downturn will prevent me from taking catastrophic losses.

Also, would it be a good idea to use a home equity loan for the 50k or does that seem like unnecessary risk since I can probably raise that 50k within one more year?

My local power company has a program where they can lower power consumption to a property(ies) to prevent the grid going down during high power usage surges. 

Moving forward blindly on that deal would have put our investors money at risk, which isn't an option, so WE took a $60k haircut to prevent that.