Despite being assured that there would be significant tax savings on my 2023 taxes, there were no cost savings or advantages to having paid $5,000 for strategy in that tax year.

I plan to be here often but have been listening to the bigger pockets podcast for the last year now, and have consistently been saving to make my first investment this year.

Just have $$ in savings

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

Could help you save some serious $$ if buying and selling there and can also get you access to their MLS systems.

Almost nobody in the Upper Peninsula has air conditioning though so maybe can save money on just doing a new furnace and not a full HVAC, we'll see.  

I'd save yourself from the headaches and just buy it with a DSCR loan.

You could also get a line of credit for about $150k (you should be able to borrow 75% of the value.)The reason I suggest this is…1) you save $40-$60k in selling costs. 2) you have a lower blended interest rate (2/3rds at 3.25% and 1/3rd at 7 or 8% instead of the whole $500k at 7 or 8%) saving you another $1k/mo in interest. 3) you only pay interest on that $150k when you actually use it, not from day 1  Unless you hate this property, or want to buy something you can’t afford without selling, that would be my plan.

Do I wait another year to save more, or do I look into a HELOC or a VA cash-out refinance? 

Health insurance payments, Health savings account lots of options.