Lauren,Thank you for your input yea I am seeing something similar at the moment basically homes I could scoop up for 500k and resale for 620k but between the rehab required and loan costs it leaves razor thin margins even with a simple 25k rehab doing work myself in SD I lose money on this due to closing costs alone. 

I like to have the lender call the listing agent directly to vouch for the pre-approval letter so they've heard a human voice and know it's not some unreachable person.As far as listing a house that needs updates, make it as clean and uncluttered as possible inside and out, we always stage (can be simple and DIY, makes a big difference) and do pro photos, and figure out what the house has going for it and what it could have that buyers love (great yard?

My simple advice is to buy it if it has real value to you and your family regardless of potential rental income.

(Keep it simple stupid) process for how they work through question 1 and question 2 step by step?

Talk to a real estate lawyer, see if they have an off-the-shelf simple purchase agreement they will tailor for your property for a reasonable fee.

My wife and I thought we had a relatively simple purchase, but we're getting caught up in some details.

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One that happened to cross my mind (which may seem silly), was somthing as simple as "What happens when someone drops a jar of pickles on the floor in a common area?" 

I've been so immersed in off market deals and making my own offers with my own Purchase Agreement, that this MLS deal with realtors seems to simple.

You could also add a simple layout to the listing.