My finances are in good condition and have a 12% DTI and about 250k to get started; would prefer to keep the first deal to under 100k if I can so I'm not putting all my eggs in one basket and if I take the 'learning loss', it won't be devastating. 

If you see errors in guest service, experience and furnishings then that is a low hanging fruit that you can easily improve on.

Yes there are issues with putting your eggs in one basket but then again I don't I have 1 area i have 4-5 areas I invest in but again they are site specific to each individual 1.

There are other lists that are easily accessible and fruitful.

Should I keep all my $eggs$ in this 1 singular basket, or diversify into many baskets? 

I am happy you took the plunge and see the fruits of your labor go further versus this over saturated and over regulated state we live in.

His channel is "The Fruitful Investor" and his name is Mat Piche. 

Those are typically "low hanging fruit" deals where the seller just wants $30,000 on a house renting for $650+, just to be done with it.

Eggs, butter, fruits, vegetables, herbs, peanut butter, many condiments, jam, honey, breads, etc can all be left unrefrigerated.

I'm inclined to put my apples in the basket @Andrew Wicklow described.