If you're comfortable posting a link to your property, it would give you more direct feedback from everyone so we can try to help you meet your target. ;-)

If I were in your shoes, I’d look into leveraging equity in your existing properties or your primary residence.

I do not have many resources, but I am comfortable taking some risk and relying on my intelligence and research.

The answer would be partially dependent on what are you looking to get out of it for rent and what type of risks are you comfortable with?

I pushed back on the idea of an up front transaction fee of 10K and told him that I'd be happy to pay a transaction fee at closing, but wouldn't feel comfortable paying 10K without it being tied to an acquisition.

Get out of your comfort zone.

Vanessa,I second others comment on the advice of putting yourself in the owner's shoes and figuring out your selling points from that point of view. 

Are you suggesting that being crammed in a small hotel room represents a better experience than being in a comfortable homey Airbnb?

Lastly, keep an open line of communication with your manager so they feel comfortable bringing up concerns or bigger repairs.

In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.