I just need a little extra help with the next steps and figuring out all of the details needed to make it happen.I would like to close on a deal by the end of this year, using either my VA loan or an FHA loan to house hack.

So you don’t get to pocked all of the extra.

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.

Those might make good rentals...but also there can be extra costs...see if they are in PIDs/PUDs or MUDs that add significant cost to the monthly payment...maybe $100-$200 extra a month.Also $2500 sounds high on rent to me for 1800sqft....I would think more like around $2000/month, but haven't looked in that area lately.I do like Forney....one issue is I don't think there are good demand drivers there. 

My rental has a lot of extra space outside around the house to consider doing a ADU build and create additional rental income.  

Otherwise, look at side jobs you can do to earn extra money. 

As an extra level of protection You could try and save up a few months of what the potential mortgage will be to give you peace of mind. 

This works well for wholesalers who sell deals to flippers, and flippers or investors can benefit even more by going the extra mile to generate their own off-market leads.

After he implemented the RUBS, he actually reduced the rent a bit to enable the user to adjust to the new extra billing.  

They quoted an umbrella policy for $200 extra, which is very reasonable.From my limited understanding of insurance policies, if I have the second-home policy with home sharing endorsement (personal liability $1M) plus an umbrella for $2M, then I should have about the same coverage I get from Proper, even in the unlikely event of an off-premise liability lawsuit.