NEWBIE LOOKING FOR ADVICE. STR, HOUSE HACK,MULTI UNIT

[Michelle Sharko]

I'm very new at this, wanting to buy another property. Was looking at multi family, STR but can't seem to find any in the surrounding burbs of St. Charles IL. or In Wisconsin where my second home is. Chicago has a few but some are not in great neighborhoods. Do you buy I'm not so good neighbor hoods?

I’m wondering about Jacksonville FL? Possibly Detroit? Detroit worries me a little, not very familiar with the area. 
Jacksonville has great townhomes with good price but not sure on the cash flow for rentals are. With Mayo Clinic there O thought it might be a good place for rentals? 

For financing which is causing me a headache!! Best ideas for FINANCING. 

Should I turn the lake house into rental property to have a better chance at getting a HELOC loan? Our DTI was 45% I do have a stock portfolio that I can draw from, they (FLAGSTAR) wanted me to take a monthly income from that to bring down the DTI but I really don't want to do that.
The second home right now is probably worth $500-$600,000 is in a gated golf community where rentals are high. No one ever sells in there. Bought it for $360k no mortgage.

I could sell but honestly we want to put it into the trust for kids so they can have it.
We are finding it difficult to get a loan without me not having income.

3. Where is the best place to start learning more? Best book, seminar, you tube, etc.. Reading David Greenes book BRRRR now.

LOOKING FOR a Hack house for my kids, rental in Florida, multi units.

I’m all over the road, I’m 56 really just want to start building more wealth before we retire. 

Any help is much appreciated 

[Ian Jimeno]

Hi Michelle!

First of all, glad you're looking into investing in Real Estate. There is a lot of benefits to owning property (cash flow, tenants pay your loan, it's a physical asset, etc.), but I think you're running into the hardest part of investing in Real Estate:

There are a lot of options to invest in RE.

This is either a blessing or curse, and your case, because there are so many options, it's a curse haha. To navigate through that trouble, pick one, figure out the numbers behind it, and COMPLETE the goal.

For instance, if you really want to take care of your kids (and have them learn the business firsthand), I would recommend finding them a house hack. You can put low money down, they learn to go through lease applications, how to manage tenants, etc. I'm currently looking for my 4th house hack, and honestly it's the best move I've ever done!

I think you should think about what to do with the second home, especially if it's worth $500k right now. Can you HELOC it and use the money towards a down payment on a rental? If so, in which market do you have an unfair advantage? I always ask my clients "Where do you have an unfair advantage?" so they don't have to start from the drawing board (which market do you know personally? Do you have a realtor/property manager there already? Are your friends investing  there?).

Be conscious: If you sell your property, that's a gnarly capital gains tax. You should educate yourself to get a 1031 exchange or invest in opportunity zones if you sell that home.

Hope this is a good starting point! Let me know if you have any other questions :)

Ian