Based on both of your posts I’ve done a little math and calculated I would have to charge $255 a night (at a 44% occupancy rate) to stand the smallest chance of making what would make this worth it to me.

Depending on the interest rate and points, this might require a broker.

Not sure if higher purchase prices/rates have created this boom or if it's that all the new supply of rentals in Chicago is aimed at top end luxury *$3000 1br type builds etc. but rents have shot up on the north side.

STR inventory in Pensacola exploded between 2020- and now which has driven down occupancy per unit and in some cases rates. 

Wanting to explore other options or find out other financial strategies for trying to build a detached home on our lot without having to refinance out of our 2.75 interest rate with a cash out or doing a HELOC.

In many cases the wire coming into the house is not rated for 200A.  

Heloc I think we could get $175k, maybe DSCR, I am a veteran with service connection disability rating 40% but with my mortgage and car loan not sure I could make debt to income work.  

I have a million classified posts showing the style we build. you'll never get the numbers at that rate. your numbers are way off and way too low. work with an experienced general contractor who knows this stuff. 

Those two together create equity.Here's what I want you to understand about “buy and hold” residential real estate:Let’s use a single family home with a property value of $300,000Let’s use an initial loan amount of $240,000Let’s use an interest rate of 7.25%And I’m going to give you $150 of cash flow per monthUse a 5% appreciation amount for your property per yearLet’s see what happens after 5 years:After 5 years…$150 of cash flow per month = $9,000Your mortgage has been paid down to $227,000 = $13,000Your property is now worth $382,000 = $82,000So that’s $9,000 of cash flow, $13,000 of principle buy down, and $82,000 of appreciation.

BTW this will also help you understand local rent rates.