You are likely going to start out by purchasing one property at a time, renovating them, and then stabilizing them, and unless you are looking to purchase in the $700k and up range, you have more than enough equity in the primary to use as your bridge financing through the HELOC... now if you are an experienced rehabber and you want to take down multiple projects at once then the $100k could get you one more property and your velocity of money would then probably be a lot higher.Ultimately, you have to do what is right for your situation and risk tolerance.

as well as what your risk tolerance and desired price points are. 

My 2 pennies:(1) I would suggest joining brew city group on facebook along with some other RE groups targeting mke area. (2) connect with other out of state investors in mke area and see what their challenges have been. (3) Linking with the right Realtor &/OR Management company is the key & they can pinpoint "lucrative" area based on your investment expectations & tolerance for risk. (4) Visit Milwaukee & Drive the neighborhoods you are considering so you can be more devoted to your investment (stay away from tough areas unless you are a seasoned investor). 

They may be the perfect investment at the perfect location, but they just didn’t fit within my comfort tolerance.

Ultimately, the decision depends on your goals, risk tolerance, and how hands-on you want to be.

Then using this you can come up with your own personal due diligence strategy (since every investor is different and has unique financial goals, financial situation and risk tolerance).

It takes a certain level of risk tolerance to do it, and a high level of local market knowledge.

Weighing costs, timelines, risks, use case, worst case scenarios, market tolerance/demand, etc should all be factored in to projections. 

While some homeowners might opt for higher insurance costs, others might seek more affordable specialized policies designed for short-term rental properties.Discussing the situation with multiple insurance agents or brokers who understand the intricacies of short-term rental arbitrage could provide tailored insights and potential solutions, helping homeowners make informed decisions about coverage that aligns with their risk tolerance and financial considerations.

Ultimately it depends on your finances and your risk tolerance, the less risky bet is to just pay it off.