The inclusion of additional units could potentially increase my qualification for higher-priced homes, contingent on the rental income they generate. 

Unless he's doing something like a big rehab to force appreciation.If he's putting down 25% now, then he should be able to refi with no additional money due in 5 years. 

@Angie Hensley, until you do something additional the LLC has no authority to sign a lease to rent out the property.

If you factor in 8% PM, 10% vacancy including economic vacancy and capex/opex of 10% (5% each), your costs (still not including T&I) would come up an additional $2016, for a total of $8895 at 1.25M and $6969 at 900K 

This can help you offset your mortgage expenses and potentially generate additional income.Explore Other Investment Opportunities: If house hacking isn't feasible or doesn't align with your goals, explore other investment opportunities in your area.

Additionally, in your experience, when is it more suitable to hire a contractor versus a handyman?

She has "trade accounts" that get her discounts as all kinds of places for materials like flooring, fixtures, cabinetry, etc, so it nearly pays for itself.

Any additional tips or things I should consider would be super helpful!

It reflects the average rental income per booked night, including nightly rates and additional fees like cleaning charges, pet fees, etc.

After a few additional email interactions that same day, your DoC stated "I do not have an answer for you.