Come to find out he actually had this issue of "never wanting to be alone" and I didn't count.  

Making it 5bd, 2 3/4 bath with a total of 1984sqft Not sure about your market but in most areas, basements do not count, its below ground level .

It doesn't count the time  spent fielding the "take me off your list calls" or the time spent with tire kickers and analyzing opportunities that weren't. 

This would count against personal use for the year.

Will having good income and credit store count for something or do I need to focus on saving?

If you are misleading someone who has a short time frame to act and you are not able to perform on the contract you are acting unethically and could do major financial harm to someone who was counting on you. you are also asking for legal troubles.

Is this because they won't count rents on the two duplexes towards your DTI?

Would we then have to acquire at least $100k in debt on the new property or does the HELOC not count toward that and we would only have to acquire at least $87k?

That's a 40% for, not counting net rental profits etc.  

Can't the income from individual room leases count when considering DTI?