Each month I have to pay the mortgage, taxes, and insurance premiums totaling $550, or $550 x 12 months = $6,600.

I send average insurance premiums out to lenders I work with but want to add more value than just that.

Fees (including points) are obvious, but lenders also can (and usually do) bump the rate a wee bit to make a "yield-spread premium" or "back-points" on the deal to further increase their profit. 

In a sense I expect to pay a premium for quality services and experience however I've yet to find that right equilibrium between price point and services I need. 

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However, that does not seem like the best area to invest given the premium home prices and less active rental market.

Has anyone had success negotiating a premium that is comparable to the local rate for airbnb's/vrbo?

., and would pay a premium to have such amenities.

If this was me, I would be at the property, getting in touch with local Facebook groups and generating bids to get handymen/local contractors taking up urgent jobs that are preventing units from being rented (even at a lower premium) that are ready to help nurse the deal.

We are selling 2 buildings this year so we will need to dump quite a bit into these 401ks to prevent our income from hitting the threshold which will trigger our paying back our health insurance premium subsidy of $18,000.