With this in mind, if you intend to leverage short-term debt (hard money), it's even more vital that your underwriting is thorough and that you have the correct systems in place to tackle potential issues.

Seems like a property that isn't going to appreciate rapidly so cashflow will be vital to its investment potential.

They care about what they estimate it would cost to rebuild the home.All else being equal, yes, older homes are more expensive to insure than newer homes for a variety of reasons. 

Here are some of its vitals:- Zestimate: $345K (I know this is typically 10% or so high)- Last Sold: 8/2021 for $281K- Roughly 1400 sqft- Some cosmetic work needed- $25K left on solar loan- The home was build in 2004 and it looks like it has the original AC unit, so I am assuming that needs to be replaced too. - 2 story house with very small rooms and and 2 steps down, imminently as you enter the front door.- Gated community and in a reasonable HOA. - The home is 2 payments behind and already got a letter from the lender about future foreclose.

A couple problems dividing a property and selling in a “Timely” manner and then picking exchange properties of equal or greater value than the lots you sale.  

You'll get a feel for the age of the neighborhoods, the vitality of the commercial buildings, the ease of location, the closeness to jobs.The markets you're describing are more linear, and usually have lower capital appreciation.

My duplex - built 1989, 2,060 sf, 2 bed/bath, 1 year old roof, value if I subdivide (county already approved) and sell each separately $150k each ($300k total)Investor duplex - built 1995, 2,300 sf, 2 bed/bath, 5 year old roof, value around $310kThe investors initial request was for an equal trade and they would pay realtor fees, which I replied wouldn't be equal due to buying/selling costs (recording fees, title insurance, closing fee, survey, inspections, loan fees, 1031 fees, accountant fees, repairs), taxes would increase due to new sale price, I'd trade a 3.75% mortgage for a higher one, and I'm on the 10th year of a 30 year loan so resetting that to a new loan would restart amortization and pay more towards interest.

The other is equally certain it will sell around 550.  

A 1031 must be for equal or greater value or the funds in excess of the value of the new purchase are taxable.

Money makes you happy only so often.But a good place to work keeps you happy every day you show up.Yes, 𝗺𝗼𝗻𝗲𝘆 plays a vital role.But 𝘸𝘩𝘦𝘳𝘦 you work?