Additionally, the contract with the wholesaler is set to expire on Monday the 27th.

I'm terrified enough of doing this out of state, so I am not interested in additional complexities with BRRRR.

For example, I see newer investors attempting wholesaling or bird-dogging for other investors to generate additional income to invest.

Your strategy takes advantage of your employment cash flow and ability to control discretionary spending.  

You can prevent this by requiring them to add you as "additional interest" on their policy.

My retirement system doesn't allow for me to roll anything over given that I'm still employed with the company and also under 59.5 years old.

I do have additional coverage for the sewer since I knew it may have issues before I bought the property. 

Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto. 

My son (age 24) however, is an independant contractor / self employed and is trying to buy a house. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.