If you can live for free and only pay utilities AND buy an investment property, that would be ideal in terms of savings and cash flow.If you can't stay and your parents want to make some money on that property, then yes, house hacking would be your best option especially since you don't want the best place in the multi.

I’m exploring all options to try to save myself.

When developing, I'd first talk with the city building/zoning about what they want to see more of and where, and try a simple project that should be smooth sailing on plan approvals, saving you time and money. 

My biggest tip is to save way more that you make and then buy a 2-4 unit building and use a 203k or homestyle renovation loan to do some rehab and add some instant equity.Also, Network as much as possible and get comfortable approach any one and asking lots of questions. 

My main concern about actual house hacking for a few years in a row is that we don't want the kiddos to have to change schools once we relocate up there.I'm thinking about getting an appreciation-oriented duplex/triplex in a pricier market with good schools that we could stay in for several years, and saving for an actual cashflow property that'd we buy as an investment property instead of a house hack.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

A moderate 80s update in Houston may not match Indy, so leaning on someone who knows the local buyer pool can save a lot of back and forth.All the best,Johnny

Additionally, we can run an automated instant valuation to save you both time and money on appraisals.Please let me know if you’re interested in getting a quote!

This will save you on subscription costs.If you want to discuss any of this further, I'm happy to answer questions and help walk you through it.Best of luck!

@Ben Cochran I hope you have factored STR tax savings into your cashflow and ROI as it can be significant.