My thought was that it would be best if she does the primary STR work and log her hours and ensure that she spends more time on the STR than I do (at least officially logged hours... since I will most likely always be thinking about the STR... haha). 

@Hieu Bui Your numbers are a bit off... roof itself will be close to $10k.. you have soffit rot and that might be rotted inside into the trusses... yikes..I saw ceilings that were leaking as well...Personally, I’d get a waste contractor bin.. remove all the crap, take a log screwdriver and then start poking around... you can see what’s not visible...Once complete, do a materials cost list.

But if “by doing” he means investing without first having the knowledge to KNOW the risks, EVALUATE the risks (and potential rewards) and to TAKE ACTION to reduce the risks then the cost of this learn by doing education is probably going to be significantly more expensive than a degree in real estate from MIT, let alone reading the\ree or four texts on your own.  

So, let’s evaluate.  

This strategy requires careful planning, from evaluating potential properties to ensuring that your rehab costs don’t spiral out of control.

You’ll want to understand key metrics like cash-on-cash return and cap rates to evaluate deals properly.For flips, it’s all about finding properties where you can add value through renovations and sell for a profit.

It allows a substantial portion of the asset's cost to be deducted in the first year of service.In 2023, the bonus depreciation rate is 80%.In 2024, it decreases to 60%.In 2025, the rate further reduces to 40%.COST SEGREGATION:Cost segregation involves dividing a property into its individual components for tax purposes.Some parts age faster, like carpets or paint.Your CPA can use this info to more accurately depreciate elements of your property leading to potential tax savings.BASIS:Your basis is the initial price that you paid for your property, including any expenses or improvements.Knowing your basis is crucial for tax purposes, as it's used to evaluate depreciation & determine the capital gains or losses if/when your property sells.LAND VALUE:This is how much your land is worth without any buildings or improvements.Land doesn't get old like buildings, so you can't depreciate it.

The financial benefit of reducing or eliminating income taxes very much out weighs the hassle and costs of a potential audit.You don't need anything fancy for a time log. 

Quote from @Paul Morton: is there an attic.. set air handler and go into ceiling with round supplies There is an attic, but I'm going to evaluate whether or not I can finish it.

As for refinancing, it is generally possible, but evaluating the costs, including closing fees and any additional points, is key.As a side note, you are obviously concerned about interest rate, and this can make a difference of hundreds dollars per month, but I see clients with properties where the monthly lease is 2x the monthly mortgage payment.