None of my family has money and they aren’t risk takers at all, so I’m starting from the bottom and trying to make something out of the generous gift from my grandparents.

I already have land w infrastructure going in for another venture and thinking about the tiny house rental on it for a temp light cash making but if you search VRBO/AirbNb for comps you’ll see they aren’t heavy cash makers, mostly due to the smaller season.  

You just aren’t as hands on. 

You should consider mailing to people who aren’t in every other investor’s sites.

Doesn't matter if the place is fully occupied, tenants will ignore the obvious issue if they aren't the one who has to pay the bill.

If there aren't any, look at 3-units and make an adjustment upwards.Residential property 4-units and under are valued by comps, not income.

If you want to incentivize the long term tenants consider $475 instead of $495, but if they have been there 10+ years they aren’t leaving regardless of rent, especially if you’re still at market rates, I mean they can’t save money by leaving right?

To make long story short she basically said “there aren’t any good deals on the market at this time”.

I also discovered that even though they have power split and two separate furnaces, they actually aren't on separate meters, so that lowered the cash flow expectations.

I'm over in the RVA area and after much searching, I've found that there aren't many, if ANY at all 3 or 4-plex's in the north/northeast RVA areas.