High bedroom counts to attract guests for weddings, families etc.

With a budget of $300K-$400K, you could potentially find single-family homes or small multi-units in those areas.I'd recommend researching rental demand near universities like Duke or NC State or even checking out neighborhoods with strong job growth near tech hubs.

I'm most interested in Single-Family or Multi-Family Homes with the intention of having Mid or Long-Term rentals (although I am not opposed to Short-Term either).

I grew up in North Florida so I have a lot of family, friends and business contacts in that area.  

I agree that is will be a gamble as to how well it will do.Also, ask the owner if they will entertain partial owner financing to keep from dragging family and friends into this risky business venture.Maybe even rent from owner for a year with right to sublease to see how it goes before committing to a purchase.

The "big" firms like AA may get a lot of hype but they generally can't compete on the next level tax strategies (Family office type strategies) nor customer service as their employee turnover is quite high.  

I don't think we are going to be able to come up with $50K before they're going to need to move and no, definitely no family members able to gift $50K. 

Investment Info:Small multi-family (2-4 units) buy & hold investment in Madison.

I currently own a single family in Akron.

We're been mostly looking at single families, but that's because we don't have a huge network yet of others interested.