I want to speak with a lender to see if we could borrow against our existing properties to put less money down, but I have no idea what the cost would be of 1) the land, 2) improvements on the land, and 3) construction of the home.

To weed people out but, the way im doing it doesn't feel very efficient. 

You need to find short-term purchase and rehab financing (i.e. hard money or private lender) to acquire and improve the property.

I did STR in a duplex starting back in 2017 and managed for others in North Conway, Ive since converted to all long term tenants and happy i did so... unless your property has something unique or a "rare" amenity.... like, sleeps 30, I honestly would not waste any energy on it in the north Conway area. so saturated, and so much big money being invested in the hotels, its tough to match amenities vs cost, and I see travelers trending back towards the hotel style accommodations. granted, for the right price, I'd buy anything and figure out what the best use for it is. use airdna.co for decent data on # of Short term rentals in any particular market. can also identify opportunities. the point of my response.... be careful in STR in any area and always have a plan B. you can change a lot of things about a property, but your cant change your basis!

I’d love to hear more about what kind of improvements were made to the property and how long the project took from purchase to sale.

Save religiously, improve your credit, and pay off any outstanding debts you may owe. 

Also, how're you improving the property while you're there to help cash flow when you move out? 

If I was going to improve on one thing, I could certainly tighten up my turnover process and make units ready to rent again a little faster or even advertise a little ahead of when they are ready.

Between forced appreciation on general improvements on the property and the capacity to add an additional residential structure, the sky was the limit on value growth.

Based on my income, I’m unable to afford a multifamily property, and the deals I’ve come across haven’t been particularly attractive.My brother, who earns $90K a year, is willing to co-sign with me, but his $100K in student loans doesn’t really improve our pre-approval prospects.