It's your gain you're essentially rolling into the new property. 

Make sure it is not a safety risk to the property or anyone else and make the best decision for your business.

But I have a kid, and hopefully and expanding family so I don't want to leave the safety of the 9-5 yet.  

Essentially being paid to live in a bigger place.

I've been doing property management for almost 15 years and screening is the most essential for making sure the tenant pays and cares for the property.

Both of those are essential to know if you want to be a good wholesaler.When I first started looking into real estate investing my first thought was to wholesale.

Thanks, @Neal Collins, you're absolutely right: I'll need to do a lot of homework on the mortgages, taxes, potential fees etc. for any given property.Another big reason I'm doing this is that there are a lot of attractive reasons to go from having an external office for my business (which is currently the case) to having an in-home office that would be tax deductible and essentially give me a discount on my house payment.However, another consideration that I must be careful of is that with seller-financing, a seller can sell the house as-is with possibly a huge number of repairs/some deeply fundamental repair needed.

So essentially if 75% of my rent covers more than my mortgage (which it does and should) then my debt to income will be lower according to lender's standards. 

She mentioned that, from a tax standpoint, if  I don't have partners on the properties that I pick up, I could essentially hold them personally.

You are essentially doing this with a duplex, and I see no reason not to do it again if you can find the right unit.