The only issue is with a bit lower rent there's a higher number of applicants that won't qualify but I don't mind the volume to get it filled. 

If you qualify, you could close on the loan in days.Home 2 could be an option for a fix-and-flip as well, but you would have to have another residence because these types of loans do not allow owner occupancy.

If you offer more $ for the property than the all cash offers AND you appear to the seller to be highly qualified in the method you are using for sourcing the payment, at some point your offer will be more appealing than the all cash offers.I don't understand why you would consider a 1031 for another property in two years. 

They have no cash to qualify for a rental or even pay for the move. 

They can qualify for a new mortgage and show they are not the ones paying on the old loan so that the payment doesn't affect their DTI.

They don't have to manage the property for you, but they can assist with getting a qualified Tenant in place. 

As already mentioned, he wouldn't be able to use rent from roommates to help qualify but based on the numbers you shared there should be a VA option available considering how much flexibility there is. 

Credit score shouldn't be the primary driver of tenant approval, because if they could qualify for a mortgage they probably wouldn't be renters.

There are a couple of unique tax laws to real estate investors - 1031 exchange, bonus depreciation on certain improvements, Qualified Opportunity Zones, real estate professional status, etc.Make sure that the accountant you interview to understand the above concepts.best of luck!

You qualify due to their experience and then now you have that experience too.