Keeping it simple with a smart TV works, but one popular streaming service could make guests feel extra taken care of without much effort on your end.Let's discuss more.

Why do you feel like you need someone to hold your hand? 

@Abel Curielthis is so beyond and more than helpful. it's been a tough gig to start, but this really simplifies it and brings me confidence.

And I guess if your always paying cash and can hold long term that might be true.. but you bring in all these payouts up front and debt behind it and that creates the risk.

I think there are two maybe 3 ways to look at this in my mind.  1) you go into it and bring it all up to modern standards but using that old charm to basically take what is there bring it up to modern standards and rent it out essentially I'm thinking cocktail bar or something trendy like that.2) most banks are on really good centrally located real estate if this is true, then I'd consider it for the dirt, plan to scrape the lot and go vertical with whatever the highest and best use is.3) a kind of combo of the two, if the lot is in a good location and its doable, pull the vaults or other "character pieces" out of the building, scrape the lot, and build whatever is best suited for the site there, but incorporate those historical pieces into the final designs.Is the site near a major retail area? 

Ideally, you'd want closer to $40k-$50k to feel truly comfortable and have a safety net for your first investment property.

I understand it’s an existing home, or older home, so I’d like to ask you to kick in $2,000 toward repairs I feel are necessary.). 

I personally feel like 30 days is more courteous but as long as they abide by state/local regulations they should be covered

Any other recommendation to ensurebthat umrella insurance is full proof and that it actually works and they dont bring that one disclaimer if and when it comes for actually paying for the insurance claim,  if ever.

- Don't click links or files if you're not expecting it or if you feel pressured to do it.