I think this because the fall is a buyers market since there are less buyers (you could get a good deal on the purchase) and the springtime in Chicagoland typically is a sellers market (you could sell for a premium) since so many buyers come in to buy.

Do yo typically get a construction loan then need to refinance out ?

You're the typical new poster here that asks for help, then gets mad when constructive feedback comes.Those questions posed will help understand where you're coming from and going.

Pretty much any way I can add value I will do it even if its a 50k house that will require that I put in hours and hours of work because investor clients are typically return customers. 

If you need the extra funds then they're already factored into your numbers and if you don't need them then you're being even more profitable. 10% in contingency is typically a pretty safe number for this.4.

Let the realtor and lender know your plan of finding a house hack - typically a duplex or fourplex but can still be done in a single family if your plan is to have roommates that live with you.

For instance, a property in Windsor Terrace purchased in the year 2000 for $140k is now worth $1.2 Million, conservatively.A more recent purchase, a Brownstone I purchased in 2015 for $900k and renovated for $300k, so all in for $1.2k is worth $2 Million now.Do keep in mind that past performance does not indicate future performance.However, these kinds of numbers are very typical from 1998 to now.When I was teaching, I used to ask my Investor Students, "What is a Bargain?"

Colorado does allow super liens, but typically, for them to remain enforceable after foreclosure, they would need to be properly filed before the foreclosure process begins.

With that being said, there are brokerages who focus on multi-family investments and those typically will focus on Duplexes and up.

Most of my customers who own their own land typically use Fannie Mae since it offers a ower Dp for 2-4 units and the guide lines are more lienant.