However, on Realtor.com for condo listings for STR here in coastal areas of Texas, the HOA fees are usually mentioned in the posting so its a little easier to get an idea of expenses..  

While the units look to cash flow, for the next 5 years we plan on using that cash flow for any extra expenses over and above what we would forecast for the maintenance, repairs, and capex items for the properties since we already have W2 jobs we plan on keeping for at least the next 5 years. 

Ensure that you market and clearly communicate your requirements to prospective candidates.

While it's not a requirement for investing, I think having a solid foundation of knowledge will set me up for success.

That type of investment works just requires prudent management to ensure you have reserves or manage cash flow to cover the winter months.

It's very expensive to hire someone to search for assets just as it's very expensive to try to collect. 

Rents don't always increase, but expenses, such as property taxes and insurance do. 

It would fix your cash flow problem, but that comes with the furnishing expenses and a little more work than long term rent. 

According to my estimates and the fact that only minor cosmetic upgrades are required, the all in cost is 30k.

Talk to a local mortgage broker about what their requirements are.