Im not quite sure how D4D can ever be outdated bc you should never assume seller thinking as to why they will or wont sell or their motivation or market knowledge.That comes down to youre ability to make a connection w seller and negotiate.

Chicago has a law that the landlord cannot deny the tenant the ability to sublet.

If you have the ability to self-educate and are pretty good at handling difficult situations, then I think you should give it a try.I do not recommend buying without a REALTOR.

Assuming there is no balloon, perhaps you could negotiate the ability to walk the 2nd on your primary to another property.

We would need to open more business cards/lines of credit to do this, and also to have ability to renovate the next place as most current cards are near limit.2) 100% on reserves! 

This is 100x more true because you're a rookie.The value you bring might be in the form of capital, experience, access to deals, the ability to put in a lot of work, social media expertise, accounting expertise, marketing expertise, etc., etc., but you have to bring SOMETHING to the table--and you have be VERY clear about what that thing is, so potential partners see a reason to partner with you. 

Your cost to entry will be lower, your rate will be lower by a third and your ability to manage the property because you live in it will be way easier as well.

I am buying a new construction primary in May and hoping for some advice prior.I have a relatively high DTI due to 7 other other conventional loans and my broker advised that a new investment prior to closing might impact my ability to close.Our goal is to do an MTR on the new property and I understand we can’t count the income towards my ratios (since it won’t be on a tax return) which is my main concern.I am wondering if buying the property in an LLC will help with the DTI issue.

At the end of closing, the cash we got back limit a little bit our ability to repeat this process.We have over $200k of equity on our primary residence after paying off our Heloc.

If I misunderstood and she's only paying you 3 months and keeping the rest, if y'all sign a termination agreement, that should give you free and clear ability to look for another tenant immediately and through end of March while already having the income from those months.If she truly is willing to pay 3 months of rent to leave, going through eviction wouldn't do anything for you financially, however it would show up on her record so other landlords know (you took one for the team).There's definitely other creative options to work through this situation with the tenant if you want to send me a PM to spitball a few