But, have you considered you will pay self-employment tax on that in April 2021? 

Not so today, but not too far away either...The biggest differences:Conventional - typically a lower rate, no prepayment penalties, backed by the government or agency, DTI, Income, restrictions on property types, restrictions on # of properties owned, require passing AUS, can be difficult for Self-Employed, and heavy Underwriting guidelines.DSCR - higher rate (normally), prepayment penalties with various structures, backed by private investors or capital funds groups, about 1/3 of the paperwork, very laxed Underwriting guidelines, usually no restrictions on # of properties owned, no DTI calcs, no Income calcs, no massive amount of TRID disclosures, etc...Cost-wise (fees and such, not rate), they are very similar. 

Can I employ some sort of a personal advisor to understand if I should buy a house or not?

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.