I have a condo in Connecticut that generates a cash flow of about $750 a month, and I have approximately $130,000 in equity at a 3.25% interest rate.

Here's the breakdown of rental income and expense analysis:1.Annual Gross Income: $25,800 (Monthly rent of $2,150 x 12)2.Annual Expenses: $25,800 * 0.40 = $10,3203.Annual NOI: $25,800 - $10,320 = $15,4804.Annual Debt Service: $10,680 (Calculated previously using a mortgage calculator with a loan of $131,775, 7.25% interest, and a 30-year term)5.DSCR: $15,480 / $10,680 = 1.45 (approximately)

Additionally, if there are any contractors in the Fort Lauderdale area who can provide an estimate or guidance on this type of conversion, I’d really appreciate the connection!

I was quoting pool prices for my clients several years ago at approximately $40K (basic package 12'X24' including screen enclosure and paver deck) and then they doubled and more after COVID.

Also, as I prepare for estimates, would be helpful to know where my in year deductions actually are.  

I'd estimate your cash flow after you pay the loan payment would be $600-$800, which a lender that understands investment real estate should give you some credit for on your DTI.As for a bank, I have a specific lender at NBI that I would recommend.

Again i believe it is my best estimate of actual sustained maintenance/cap ex in my market.I did an estimate about 1,5 years ago on a emerald coast 3/2 condo with class a interior finishes and came up with $300 for just the interior (class a finishes cost more).  

Price out as much as you can in terms of materials and estimates.

Estimated costs range from $500–$1,000 annually, depending on the complexity of their LLC and rental activity.For Partner 2 ($148K joint income, W-2, 1099 income, 1 rental, 2 kids), a CPA is strongly recommended.

See the chart from Fair Isaac Company (FICO) below: FICO Score Pct of Population Default Probability 800 or more 13.00% 1.00% 750-799 27.00% 1.00% 700-749 18.00% 4.40% 650-699 15.00% 8.90% 600-649 12.00% 15.80% 550-599 8.00% 22.50% 500-549 5.00% 28.40% Less than 499 2.00% 41.00% Source: Fair Isaac CompanyAccording to this chart, investors should use corresponding vacancy+tenant-nonperformance factors of approximately 5% for Class A rentals, 10% for Class B and 20% for Class C.To address Class C payment challenges, many industry "experts" are now selling programs to newbie investors about how Section 8 tenants are the cure.