This is completely up to you, If an individual came around with perfect credit and met your other income requirements I assume you would rent to that person.

I have till mid-late 2025 to sell without capital gains tax (< $500,000 couple).I'm trying to figure out how to improve the performance of this property and have some thoughts about it, but would love to get feedback from other REIs.Option 1Add a ~800 sqft ADU in the backyard which I think costs ~$250/sqft (total $200,000) and I think could rent ~$2,000/month.

You would have more fun performing your own open heart surgery than you would dealing with Caliber. 

I am looking for a bank that holds tenants security deposits and automatically pays the interest directly to the tenant annually, see the rest for description.Hello, I am a first time property owner and am trying to figure out where it is best to deposit security deposits, I am aware that it must be deposited in an interest bearing account per MASS law but also the tenant needs to receive the interest annually and I do not want to have to manually perform this task.

 I personally never listened to him.. what was it that you liked about him ? 

but it takes time and effort - like going to the market IN PERSON, and setting up a team IN PERSON. 

I've seen some posts both here on BP, in local FB groups, and heard comments in person corroborate this.

Only the person running the club chooses potential investments.

But since that is the choice you have made: I don't know what it is like in Pueblo; but in Mesa County where I live there is a person on staff that walks you through the process and the necessary paperwork that needs to be filed (they don't fill it out for you - just provide the steps).

Whether that be starting the side hustle of real estate investing, or finding a new job, but, personally, I would not suggest you leave a well paying job until you have started down the path of real estate investing on the side.