Questions to ask at Showing/Estimating Cap Ex

[Ryan Newport]

Hey all, 

So I got pre-approved and I'm going to start actually heading to some properties. 

Brief of investment target: I'm targeting 2-3 unit MF own-occupied house-hack for my first investment property. It needs to cut expenses down to a minimum while living in, and create positive cash flow for years to come. I'm using an FHA with low down, so for more than one reason I'm planning to hold the property for a good number of years. I've vetted out the areas I'm willing to invest in and I've gotten a solid handle on what rents are running for in each market based on bedroom and condition. But I want to make sure to stay ahead of the game and make sure nothing bites me down the road. So with that being said I'm looking for 2 things here that sort of overlay each other.

1. What questions should I be making sure to ask at a showing? Questions I should be asking the owner, my agent, the landlord, myself? A list of the questions that you make sure to ask would be very helpful. 

2. I'd like to be able to estimate my Cap Ex, and how much I should be appropriately setting aside monthly. I know some people do a percentage of gross rent, but I personally feel a bit more compelled to actually spreadsheet out all the items and come up with a more definite number. I think visually it just makes more sense for me this way too. Combining the first question with this concern, what should I be making sure to check on to be able to most accurately create said spreadsheet. 

All insight, personal experiences, documents, and suggestions are very appreciated! TIA :)