I have mowed and taken care of the lot all 8 years we have lived here and it has lived as if we have one acre with our house.Question: if we sell the house to one party and the lot to another do both qualify for the primary residence capital gains exemption?

You'll want to talk to a few local lenders to get a better idea what you'll qualify for and what the terms of the loans are.4.

I'm not a lender but I'm sure once they obtain more information from a buyer & ask the right questions they have a pretty good idea who is qualified and who is not.

I don't even agree with cashing out equity on Property A so you can qualify for a loan on Property B.

I was pre qualified for a DSCR Loan shortly after buying my first house but due to financial constraints to come up with 20-25% of the down payment I feel like I’m stuck.

With the addition of the Qualified Intermediary whose only role is the administration of the 1031 exchange. 

I was under the assumption that I needed much more hands on experience but have since been told that the 6 years I owned a GC company would qualify. 

I've had multiple qualified applicants.  

If you don't have a qualified HVAC guy or he can't find the issue you should get another one in. 

As long as there is a qualified tenant under good management then there will be cash flow to service expenses and that service.