Should we pursue a "cheap" rental in order to build rental history in the hopes of securing DSCR loans down the road? 

Of course the rate is higher with 15% down, but it helps investors get that property secured with less out of pocket.Happy to help if there's anything you need.

Anyone over 18 fills out has to furnish their social security and driver's license numbers, and pays a fee for a credit / background check.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

I was thinking of giving him 3 options.Option 1: He switches to a month to month lease changing to a weekly rent rather than monthly, the new lease will have different rules (ex. such as agreeing to a cleaning schedule and a liter schedule or trash needs to be picked up and placed in a trash can every 12 hours, human waste can not be stored in containers)Option 2: He moves out at the end of March, I keep the security deposit as rent and he does not have to pay February's rent and late fees.Option 3: I'll give him $400 to move out 3 days after we have this discussion.Thank you for any suggestions, I would like to handle this delicately as I don't want a squatter living with me.

In contrast, a traditional TN LLC may face challenges due to limited charging order protection, potentially making it less secure against creditor actions.To address these concerns, some investors use a two-tier structure where a TN LLC—holding the property—is owned by a Wyoming holding LLC, benefiting from stronger asset protection laws.

Add a Rental Security provision to receive stock options in Lazy Dogs LLC for any upside when it goes public!

You can not do a pet deposit unless your security deposit is less then 1 months rent.

I'd say start the process of securing your HELOC if you havn't done so and spend time analyzing deals and determining what type of investor you are looking to be. 

Running the numbers on paper is one thing, but actually securing bookings at your target rate is another.Sounds like you’ve got a good handle on your market and what your guests are looking for, which is key.