From there I'd look to refi and use the cash to then acquire STR's or potentially bigger multi-family/apartments.

While we both have strong W-2 incomes, the large number of properties I own has made conventional lenders and agents caution that securing a loan for our primary residence could be a highly complex process.I’ve consulted with some local banks I work with, and one has expressed potential interest in financing our primary home.

The current use of the property as a two-family dwelling significantly impacts its value and marketability, which is distinct from single-family homes.The initial appraisal comparing your property to single-family homes is likely an oversight, as multifamily properties are evaluated differently due to factors like rental income potential and investor interest.

I am afraid we will fall for a property with a false sense of a good deal.Are there any suggestions to help me run an analysis that would better account for the larger down payment and allow me to better analyze potential properties in the future.

Many of my deals were priced properly, but often the seller or market can't for various reasons see the potential in the property. 

You just get penalized and lose your potential guests by doing that which is the whole point of being on multiple platforms.

buying 1-2 rentals that break even/have a little cash flow would be my choice given that I'm able to save 100k a year and potentially have cash flow from my rentals, means I'd still be able to pay my mortgage on the primary and the rentals.

Effective  12/1/2024 @ 12:01a the Louisville rental registry requires the 16 page Lead Hazard Evaluation form in addition to the Affidavit of Compliance.

I guess for me the dividing line is does it damage the function or cause a safety hazard if I leave it on the tenant.  

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!