If you don't have a crazy house like a potato, a tremendous view or historical area, then choosing a pic is harder.I like the idea of the game room if that is your best feature.

FinancingADUs are rather difficult to finance historically, but that is getting somewhat easier.

The sellers were only taking cash offers so we didn't look into SBA financing, but I think it would have been hard to do since there wasn't the right amount of historical cash flow.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Be kind to yourself and feel free to send me a DM if you think that I can be helpful resource.That makes sense but yes I do have FOMO, house prices have historically increased faster than rents, thats a nation wide trend.

I also agree that RE appreciation is unlikely to match the last dozen years, but you never know.Where I am unsure we agree is that paying $450k to improve the cash flow ~$3k (your numbers but I expect my delta wold be similar meaning both my cash flow estimates would be worse than yours but both would be worse by the same amount not affecting the difference) makes sense especially if the cost of having the extra $450k is only 6% rate which is historically simple to beat via numerous investment options and hopefully no one is investing in RE for an expected of 6%.  

I would think your insurance agent might have access to some historical information for a specific area as they would want to examine this closely for their underwriting.

I have two properties in the Blue Hills area, which have historically done well. 

@Jonathan Greene I'm not sure what you mean by "most will not cash flow as an out-of-country investor" as it might suggest that the cash-flow of a given property has something to do with the nationality or residence of the owner but, in any case, you're absolutely correct that, historically, the net rental yields of LTRs in US cash-flow markets like the Mid-West have been typically higher than in the average European market, although that wouldn't be the case for many other US markets like California or New York.

Selling a property that requires significant work can indeed be challenging, but there are several avenues you might consider exploring:Local Real Estate Agents: A local agent with experience in selling fixer-upper properties or historical homes in your area could provide valuable insights.