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All Forum Posts by: Chris Winslow

Chris Winslow has started 6 posts and replied 98 times.

Post: What makes you take the chance on a new lender?

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@Kate Glassman

Definitely by asking around and referrals from other investors would be number 1.

Assuming that nobody you know has worked with them then ask them about their basic loan terms and types of loans they offer. Definitely ask about the types of clients they typically work with and what they do for them.

Make sure that you have a base knowledge and understanding of some of the things that you would be looking for in a lender so you can ask them those types of questions and see how they answer. After feeling them out on the phone, it should give you a pretty good idea of they seem legit, I also helps to talk to a few other lenders if there are other ones offering the products that you need. Good luck!

Post: Thinking about renting out current SF and House Hacking a MF...

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@Ray Fajardo

I think that sounds like a great idea as long as they will cash flow, run some calculations in the sf, you can use the BP calculators for a few times for free and they'll make sure you don't miss anything. As far as starting with a 4-plex, that'll be the max you can do as a true 'house hack' with a normal low down payment loan such as FHA.

Starting at this size also allows you to gain some experience before jumping in too far and feeling overwhelmed, 2-4 units are great real estate 'training wheels.' Going above 4 units changes your financing options a lot and how properties are valued so make sure to look into that before jumping in.

Good luck with it! Get some base knowledge, connect with local investors, realtors, and lenders, analyze lots of deals to spot a good one and go for it!

Post: Looking to hopefully connect!

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@Marcus Joseph welcome to BP, I'm not in your area but feel free to reach out if needed, good luck starting out, definitely get out there and make some local connections! 🤘

Post: Help with next FHA or VA loan

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@Richard Pina

Congrats on the first purchase, that's awesome!

I am not a lender so don't have the exact answers but can provide some input.

Yes that is the case that you can only have 1 FHA loan at a time. I have heard of some specific situations where you are able to have 2 but that would probably be difficult to get with most lenders.

For VA loans if you're talking 2-4 multifamily and plan on owner-occupying the building then that should be okay since it sounds like you are past you required owner occupy period for FHA and I don't believe having an FHA loan would affect the VA loan.

Good luck!

Post: New to Forum Introduction

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@Michael Voss awesome to have you in the community, BP is great!

Hi Ronaldo! There are definitely people that make nice returns on the South and West sides of Chicago, I do agree that it would be a very good idea to get the opinion of someone with boots on the ground in those areas as it can be block to block. For the western suburbs you mentioned, I hardly ever see something that pencils out for me in Oak Park, Berwyn can be good but deals are getting harder to find, Cicero can be good for sure for numbers but it’s more C class.

One big benefit of being in the city proper is that taxes are way lower than in the burbs. As far as appreciation vs the suburbs I think it really depends on which specific neighborhoods you’re looking at.

Personally, I think the near west suburbs are great buy and hold areas. You could also look into La Grange, Lyons, Forest Park, and Brookfield. I don’t have personal data on the total term that tenants rent for a 2 vs 3 unit but I would pick a 3 if possible because generally it pencils better and I don’t think there is a big difference in tenant quality.

I have a place in Berwyn and Little Village (west side of the city proper) so happy to help if I can but I’m still new, I highly recommend you to connect with @John Warren who owns and manages a bunch of units around the area!

Post: Starting To Plan Out My REI Journey and Asking if I'm Crazy

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

That's awesome that you are thinking of getting started, definitely do it!! As I am sure you have heard, house hacking is an amazing way to start and there are a few good areas in Chicago that work well.

First for Jobs- Check with GC Realty, @Mark Ainley would be amazing to learn from (also hosts one of the events below with @Tom Shallcross), here is the link for their jobs:

https://www.gcrealtyinc.com/ca...


My guess is you may be too early on in being able to get something under contract immediately without having an income history but it's not too early to start connecting with lenders, investors, and realtors, and learning about which areas and types of deals would make sense for you. 

My recommendation is to connect with local investors at meetups, get to know a few people, and get a feel for what they are doing and in what areas. Here are a few places to connect, there are 3 awesome meetups coming up:

- Chicago West Suburban Real Estate Investors Meetup https://www.eventbrite.com/e/f... 

- Straight Up Chicago Investor Networking Event: https://www.straightupchicagoi... 

- Chicago RE Investor Meetup with @Jonathan Klemm https://www.biggerpockets.com/...


Connect with a local realtor and lender that can help you strategize and see what makes sense for your situation. I use @John Warren as my realtor and couldn't ask for a better team, you'll learn a ton just from one conversation (I certainly have over the last couple years). I use @Zack Karp as my lender and they rock as well, smart, creative, always willing to help, and very professional in loan processing.


If you get set up with a couple of good connections then everything in the process will be smooth from selecting an area and strategy up to closing on your first deal. Good luck!

Post: Chicago West Suburban Real Estate Investor's Meetup

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

Heck yeah, looking forward to it!!

Post: Chicago Apartment Syndication

Chris WinslowPosted
  • Investor
  • Berwyn, IL
  • Posts 104
  • Votes 71

@N'Dambi Adonis and this one with @John Warren Check out Chicago West Suburban Real Estate Investors Meetup https://meetu.ps/c/3WwBk/FJVzz/d on Meetup