I've been living in my current house hack for ~1.5, and I placed my tenants in September 2023 (lease is up at the end of August).

Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

I work in group home settings for a living and at my previous facility there were two clients per bedroom which would give you potentially 8 in your house while at my current job there is one client per bedroom which would only be 4 clients in your home.

I live in MA and I know it is a nightmare to deal with tenant here.

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

Quote from @Vince Scipione: Yes, they are a popular choice where I live and work, however with the ever fluctuating cost of oil heat, many people have swapped over their boilers/furnaces to what is called a "Propane Gun" essentially it is a device that is affixed to the front of the furnace/boiler that injects the propane and ignites it.

Good to know as I have a property coming on the market and we had one off market offer already all cash but at 10% list price discount (which we most likely will reject).Curious if you think the california fires will assist the market since many of those people need places to live for years and I am guessing some will flee california?

Will be difficult because you currently live in the property . is the 2nd unit livable and just looking to renovate ? 

Clean water, air, peace and sunshine are nature's remedies and in over-abundance on the Oregon Coast. 

Too bad you can't buy something owner-occupied, put 5% down with the best interest rate, live in it for 12 months (and fix it up), rent it out and repeat the cycle.Here's some other info you might find useful:----------------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?