See if you need to save up some money for the lease extension and any mortgage paydown to lower LTV and start saving now. 15 year primary term lease can be way more valuable.

It's crucial to evaluate how the deal performs with the new mortgage:Updated Financials After Refinancing: Market Value: $459,000 Mortgage Amount (80% LTV): $367,200 Equity: $91,800 Interest Rate: 5% (30-Year Amortization) Assuming after 12months the rate will drop to 5%Monthly Expenses: Mortgage Payment (5% Interest): $1,971 (Now you are paying interest and principals) Property Tax: $260 (assuming has been increased with a 4% from last year) Utilities: $361 Insurance: $104 (+4% Adjustment) Vacancy: $166 (now after 12 months we can assume we have some vacancy at 5% factor on annual rent) Repairs & Maintenance: $166 (now after 12 months we can assume we have repairs at 5% factor on annual rent) Total Monthly Expenses: $3,028Rent Income after 12 months assuming annual rent increase at 5% : $3,323Cash Flow: $295$ per month 😊Long-Term Gains: $5,418 Principal Paydown year 2 (this will increase each as you pay off your mortgage $36,720 Property Appreciation (assuming 8% per year) $3,540 Cash Flow (this will increase as rents rise)Total Annual Return on Investment: $45,678 with just $ $22,789 remaining in the deal.

It looks like it could deliver a 7% gain. 

It has gained a lot of interest from millennials and Gen Z in the last few years in particular.

I might also consider if i could turn the garage into a rental, or into an apartment for me, while renting the other place so that I'd still be on the property at least until I gained confidence in the tenant.

They are unparalleled and I gain so much from them!

Recommended Long term rentals are the way to go at first, Medium term and short term are strategies to look into though once you gain your bearing.

.- Selling could yield $400-$600k, mostly tax-free, if sold by spring 2025 while within the 2 of 5-year capital gains exemption.Options:1.)

If married you can exclude $250,000 each in capital gains if your primary residence.  

But, like others noted, courses can only be even remotely valuable if you actually know what you want to do.