I'm a local investor, flipper, and property management company owner.  

I ended up getting around 9 deals under-contract, while constantly being pressured by my manager to get more deals under-contract or he would publicly mock us in front of everybody.

I am just saying if I managed your property, I would never paid for the damage out of my pocket simply because I have a solid system and team to win any reimbursement cases. 

You can manage your risk. 

Last thing, I would strongly consider consulting with a knowledgeable property manager or attorney once you have a copy of the current lease and all of the facts.

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

For the property I purchase, I’d like to keep my monthly mortgage payments at $2,000 or less.I prefer a turn-key property since this is my first rental, and I want to start generating monthly cash flow immediately without the delay of repairs or managing two mortgages.

These homes were built in 2016/17 and I've managed/maintained them myself.

It would be far better for you to join NARPM - National Association of Residential Property Managers SE Virginia Chapter and join as an affiliate. 

I have a feeling just starting out my home is not going to get much exposure on sites like air bnb or vrbo until I get some good reviews.If anyone has experience in this market I would be intrigued to hear how best to manage my new STR.