If you just completed the renovation, most lenders are going to want to see the property seasoned for 3-6 months and rented before they look at doing a refinance.

Google search for an IRR calculator and it should be simple.As soon as the condo seasons in 6 months, do a cash out refi and re-deploy the money to scale your portfolio.

What is something you wish you would’ve known before getting licensed in RE?

It is not something to rely on as STR especially are unpredictable in their revenue and is highly seasonal.

Look for a lot of people looking for deep clean jobs as we move to tax season.

I think we're going to go with the gift certificate idea... feels fitting during the holiday season and also appropriate given the amount of time she scheduled around being home to let workers in the house, etc.

Of course I know this is business and I have to put my feeling asideI guess what Im looking for is some words of advice from seasoned investors who have dealt with similar situations and to help me get a different perspective on how to approach this mentally and see it more intuitively than emotionally.

Most lenders are doing 75% for refi, local banks can possibly do 80%.Down payment 15%: $30,000Closing Costs for hard money: $10,000Closing costs for refi: $10,000~Loan Amount: $230,000Cashout Refi 75% LTV: $265,000 (Get after 6 months seasoning)Monthly Payment: $2210.72Rent: $2,800.00Cashflow: $80~ after Capex, repairs, vacancyTotal Money In: $50,000~Just my two cents. 

There are "professional tenants" out there that can tell if you're a seasoned pro or on your first property.

This is not a bad deal you've outlined, but not a good one either.Most seasoned investors look for properties that they can either:1) Get below market price2) Get seller financing3) Can somehow "reposition" via cost-effective improvements for higher rents, or adding a unitWith the market cooling off, you should find more and better deals.