All Forum Posts by: Satish Subramanian

Hmm.. seems BP bugged and duplicated my post. Anyone know how to delete a post?

Welcome to BP Chris. I started on the same track as you (normal full-time career in Chicago + house hacking) in March and it took a lot to get just to where I am today: Closing on a 3-flat on the NW side on Monday.

My only advice is to get going today! If you need the REIA's and mentors to start, go for it. But seeing as you're in FinTech, I can't imagine you need it if you just read a few of the basic real estate investing books and run calculations on a few postings.

It took me over 100 deal analyses online, 15 in-person visits, and the process of buying in Chicago in this market for me was brutal. Start today, one step at a time, learn through the process, and keep after it.

Also, I realize I'm not the most seasoned person, but I do have some references for people that helped me along the way, and I'm definitely happy with them so far and am willing to share.

If I buy a 3-flat in Chicago and live in the top unit, can I depreciate the entire building normally as I would as if I was an investor who did not live in? If not, would I be able to depreciate 2/3 of the building?

I'm trying to decide between 2 options: 

1) live in for 2 years and then sell within 5 years, to avoid paying capital gains

2) live in for 1 year, keep as a longterm rental, and then buy another place to house hack in

Any advice/recommendation on this decision?

Welcome to BP! I'm curious to see how you go forward. Are you thinking of staying in the South Side with your investments or go somewhere else in city?

Either way, good luck!

Welcome to BP! There’s plenty of info on here and great recommendations on books to read for more info. As an example, It took me only 3 months between starting to learn and going under contract for my first rental property. Good luck!

How you finance it, although important, is probably less important than the cash flow/potential appreciation numbers of the property itself. If it’s not a good deal, the issue of leveraging or buying straight out won’t be the real issue.

@Dan Razowsky We might as well be the same person. I'm currently renting Logan Square until closing as well. I also am working with Sam Sharpe on the loan side, but I had to put 20% down (my credit score wasn't great, so maybe your situation might be different). Do you already have pre-approval from Guaranteed Rate? On the place I'm under contract for, that pre-approval is what helped me win a multiple offer situation.

I was looking all the way from Logan Sqaure to Jefferson Park near the blue line, but not much was available with positive cash flow. Good luck! I'll send you a connection invite. I'm sure we'll cross paths or be able to learn from each other as we go down similar paths.

I’m no expert, but if you owe more than it’s current market value, then I’m inferring that this property has depreciated in value since you bought it. Also, the repairs and vacancy that inevitably come with operating rentals mean a negative cash flow. Negative cash flow + low chance of appreciation = yikes. Without knowing anything else, I’d strongly consider selling if you have a offer that’s higher than market value.

Im soon to be closing on a 3-flat in Jefferson Park. I’ll be house hacking and it’s only one property of few I’ve seen in the past 3 months in my desired area that will cash flow positive. Before offering on this place, I looked at 15 in person after god knows how many online. The only words of wisdom I can offer is to not give up and be prepared to turn in an offer the moment you find a “deal”. Mine had 2 offers by day 4 after listing. Don’t settle and keep at it. You got this!

@Justin Poulsen - Thanks! I have been renting in Bucktown and Logan Square for the past 2 years, and the growth along the blue line corridor is for sure real. The place I am buying is 10 minutes walking from the Metra & CTA, so really hoping the announced investment in that station is going to spur more growth as well.