What can individuals who are in that position do to make a lender more comfortable, or is it just going to be accepting higher rates?

Be comfortable saying 'no' to business you can't take on and manage effectively.

Are you comfortable with qualification on DTI / personal financials?

I just haven't done enough research on refinancing and seller financing to feel comfortable.

You want an unbiased Inspector.Then:1) Do a SWOT analysis of your resources2) Write down your real estate goals3) Pick an asset type: SFH, 2-4 units, 5+ units, or something else like MHP. 4) Pick an asset class: Class A, B, C & D properties, research pros & cons, pick one to focus on5) Pick a real estate market that matches your resources & goals6) Contact local agents & PMC’s to start sending you listings to analyze7) Analyze a few deals weekly, get comfortable with the market and refine what you're looking for

(4) Am I comfortable investing in a saturated market with my first STR?

If you feel confident that your income can 'comfortably' cover the debt then it is your friend and another source of funds.

Does your agent have the connections that can assist and will they provide updates via photo and video 2-3x a week to keep you comfortable?

I am ready to leave the educational phase, even though it is really comfortable, and want to put my first deal together.

You go there at night and you feel comfortable going into your building in the dark.