Wholesaling will naturally connect you with other investors since that is who you will typically be wholesaling to.

A couple answers to your inquiries:In talking about $1M growing to $4M, I do mean that one must be more active than buying a single property and waiting for natural appreciation.

If you hang around people who are doing what you want to do, then naturally you will eventually follow suit.

Trying to avoid Chicago due to price point and the tenant-friendly nature.

For Conventional, you put the 5% down, and either make improvements to the house to increase its value or just wait until you pay down some mortgage + the house appreciates naturally and it gives you an extra $100-$125 in cash flow every month when it drops off. 

It's likely that things are hidden behind the walls as well since an inspection is visual in nature only.

In addition, in the same chapter the authors say to "Watch Others" that "by associating with investors who are involved in the same kind of investing you want to get into, you will naturally begin to pick up on the traits that make them successful".

He's already lived 6 years longer than his father did, and his wife's had cancer twice. 

Spoke with my lender about the best strategy to complete this, and refinancing the original purchase into a conventional loan seems to be the best way to go about this for several reasons:1) You can take advantage of unforced (market) appreciation2) Longer time to pay down equity naturally simply from occupying.3) High rent appreciation after refinancing and renting4) Can take advantage of tax benefits if you sell later on down the road since you occupied as your primary residenceNow for you if you have equity in the 15-20% threshold from mainly appreciation or principal paydown, I would consider looking to refinance into a conventional loan so you have even more VA eligibility.

She said she wants to sale a the home she raised her kids in, which she had given to her son that about a year and a half ago past from cancer.