An offer of $34.95M negotiated up to $35M would actually put the seller down -$95k net versus accepting the initial offer. 

Obviously, if your prepayment penalty has already expired, this is not an issue.Personally, I'd keep the extra funds and use for other investments that will potentially turn into more revenue versus paying extra on a loan that will take years to potentially realize the savings...Cheers!

That's why we have Freedom of Speech, versus tyranny where people get their heads cut off if they speak unpopular things.

For example, for rental properties, lots of the categorization depends on the REI's specific tax strategy regarding what we're capitalizing versus what we're immediately deducting.

Always happy to see new investors jumping into action versus standing on the sidelines.  

As for the move-in fee versus security deposit issue, many landlords prefer security deposits for better protection, despite the extra steps required in Illinois.

@Alec Barnes one of the problems with communication is the different expectations.Agents and consumers all think PMCs should be available 24/7.NOT POSSIBLE for the relatively small monthly fees owners pay PMCs versus the thousands of dollars of commissions agents get per transaction.So, while agents may answer their phones 24/7, most PMCs do not.

Also adding in here for anyone else viewing that we would need to consider the possibility of the IRS classifying this as a second home versus an investment property and disallowing any potential 1031 exchange due to allowing a family member to use the home rent-free.There are safe harbors to qualify for a 1031 exchange.

Honestly there are several career paths that will help (Renovation contractor, real estate agent, corporate RE analyst)  but depending upon whether you are looking for a career investing/flipping versus using your W-2 career income to build more by flipping, you can approach it better in my opinion by learning through doing.Flipping especially 1 at a time isn't a full time job and my thought is that you get help on your first, maybe first few flips. 

I would say take a deeper dive into the nearby product and see if there is a premium in rents for a duplex unit versus an apartment.