There are a bunch of different "conventional" loans, and as it sounds like you're finding out the down payment is very different if you're planning on using it as a primary residence vs. investment.

Another had a main sewer line backup into a basement.

The city has a big improvement plan (working to bring more jobs & biotech around the health district it’s in) that’s being enacted, the neighborhood also has one that’s not yet being done.

Plan ahead if you buy in a seasonal area.

To mitigate this, I've devised a plan that involves leveraging my primary residence.I've been residing in my current home for the past five years, which I secured at a very favorable interest rate.

Planning to occupy one of the units and use the other one as STR.

The tenant should try a level billing plan and if they are qualified for any assistance. 

The process can be started about a month prior planning for a 30 day close. 

Talk to her and find out what her plan is, but remind her you need to get paid.

it's possible but unlikely. a great CPA who specializes in REI will be able to help you plan AHEAD for tax time and use different pieces of the tax code to your advantage, based on your unique situation, and ultimately save you way more in the long run. would you rather pay $750 to have a return done & get a $5,000 return, or pay $30 to have a return done and owe $5,000?