Would this be an issue especially since I would not have been employed at this new company/job for at least 2 years?

They do not currently have any type of employment.

Its probably too late for your first sale but before you close on the second sale consider doing a 1031 exchange so you don't give away as much of your profit to your employer(Uncle Sam).

Many of these markets had vacation rentals long before airbnb so risk of regulation is low, and demand should continue to be strong as more Americans migrate to the south for employment and housing opportunity. 

I managed to save up $100k to invest and have decided that I will no longer contribute more than my employer match (4%).

Hi BP members, I'm new to the forum and the field as well but I've begun listening to the podcasts and am trying to gather as much knowledge as I can before jumping into the deep end of real estate investing! I've liv...

When evaluating a market for multifamily investments, one particularly important factor to analyze is employment trends.

Classic bait and switch. 

Categories include: personal references, employers, and landlords?

To name a few that we've seen...10% down P&L, Bank satement & 1099 loans up to $3,000,000 : these are products that require no tax returns to qualify, these can potentially provide much more leverage to  self employed buyers3.5% down jumbo loans up to $1,500,000 with NO PMI.