These are questions that have stayed in my mind through every episode I've listened to.

(I was a stay at home mom when I did my last big project, and really had all the time in the world.)

You have to purchase in cash and you can only stay in them 28 days per year because the HOA runs it like a business and leases the HRH name but you do own the deed.

We are in winter so hate to have the property stay vacant.  

If you can get hold of a reliable and honest builder, you will be fine (that does not mean you will not go over budget).Low CapEx, Little Hassle, Quality Tenant, You can manage new construction out of state for the first 5-years, Tenant May Stay longer (because is a brand new house) are few benefits of new construction.You may not be able to get close to the 1% rule though.Goodluck

I tell every Chicago investor who calls me about Milwaukee to stay in Chicago - the economic delta is just not big enough to take on the remote cost and efficiency burden.

We see many travel or remote workers looking for flexibility with their stays, such as healthcare workers. 

I only mention this because I noticed your mention of Furnished Finder, which is the only platform I list my MTR, and FF caters to 30+ day stays. 

For 2025 we are assuming it will rise at $1500-1600Same townhomes pending at $260’s; if we upgrade kitchen/bathroom around $275 upCurrent tenant leaves Dec 31, 2024 Assuming rent stays the same for LTR, we will be cashflow negative since Home/Hazard Insurance and Taxes will increase inevitably.Should we:1.

Structuring your lease in this way would benefit you by 1) locking in a longer term contract to avoid turnover costs and vacancy loss; 2) it moves your lease end date out of the winter season and into spring/summer of 2026 so it can be more easily marketed and re-rented to match the seasonal demand cycle; and 3) it avoids any upset/angry tenants who may have been incorrectly assuming their rent was going to stay in the $1,200 range after their first 6-month lease term.Would love to hear any updates you have on how this one shakes out for you though!