Hello everyone!
I am a property manager in Chicago. We currently hire building engineers and pay a monthly fee for them to do maintenance on the building ( go check out maintenance work orders, etc.). The are technic...

I would really like to scale my business in the next 18 months and would like to know how others have gone about it.

You might try to find something with more doors so you can get some economy of scale.

To help with this I have include below a map containing risk scores for areas within Milwaukee.The scale is A to F and is generated by comparing eight different market risk indicators.

Vacation rentals can be amazing investments, but they are also small businesses, so be prepared for that.Lack of a mortgage is great for a single property, but think about your time horizon and if/how you want to scale.  

The rating scale is not formal, it would not be on an assessment, it's just based on your feeling when you know an area well. 

@Geoffrey Morales also depends on your experience, the scope of work, how much time you have to dedicate to the process.Best and fastest way to scale is using turn key with GC.

Can you scale it up and out? 

With the cost of construction that you mentioned, it doesn't seem feasible to make affordable housing in most markets.MF in Portland these days are all up scale and cost 400 a foot to build.. and rent for about 2 to 2500 per 1K sq ft. govmit wants affordable housing they need to open up the tax credit vaults.. also in this market  a new ordinance pass requiring a certain amount of low income units per project there was a rush to get projects through before the ordinance and since that time new projects have dried up to a trickle. 

Ultimately hotels have scale which will always give them an advantage.