I remember visiting a buddy’s place in Austin years back..he had a similar setup over his detached garage and was convinced that adding a window unit and some carpet would let him count that space towards the home’s total square footage.

Also consider adding higher end finishes in the bathroom(s).

It's an agency, and I could invest in ads to drive more business.. in theory the return there would blow the return of rentals out of the park. 

All they are doing is adding additional costs and getting zero protection.

Then they won't need an upfront payment for work they haven't provided yet.Also, get a signed contract, copy of the drivers license, contractor's license and be added to their liability insurance.

If you added in the cash you should have to protect against contingencies, the actual return goes down (or the risk sykrockets, your choice)- If the $300K properties cashflow, definitely a better bet. 

If you DM me your email address I'll get you added to our events email list.Regarding the options you listed, I think #1 is best.

Value was added by leveraging the property’s desirable location and Erika’s deep market knowledge.

His listings were mostly on nystatemls but have begun creeping up on all the other major sites.One of the properties he listed is NOT for sale according to the owner and I suspect that to be the case for many others. 

Maybe adding a parent a lease co-signer (and payer) might help.